DE2260576A1 - PHOSPHORIC ACID IMIDATE DERIVATIVES AND PESTICIDES CONTAINING THE SAME - Google Patents
PHOSPHORIC ACID IMIDATE DERIVATIVES AND PESTICIDES CONTAINING THE SAMEInfo
- Publication number
- DE2260576A1 DE2260576A1 DE2260576A DE2260576A DE2260576A1 DE 2260576 A1 DE2260576 A1 DE 2260576A1 DE 2260576 A DE2260576 A DE 2260576A DE 2260576 A DE2260576 A DE 2260576A DE 2260576 A1 DE2260576 A1 DE 2260576A1
- Authority
- DE
- Germany
- Prior art keywords
- compound according
- och
- sch
- carbon atoms
- radical
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000575 pesticide Substances 0.000 title claims description 4
- -1 PHOSPHORIC ACID IMIDATE DERIVATIVES Chemical class 0.000 title description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 title description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000002917 insecticide Substances 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 239000000642 acaricide Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 230000001476 alcoholic effect Effects 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 241000238657 Blattella germanica Species 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- 239000003053 toxin Substances 0.000 description 4
- 231100000765 toxin Toxicity 0.000 description 4
- 239000004744 fabric Substances 0.000 description 3
- 241001425390 Aphis fabae Species 0.000 description 2
- 229920000298 Cellophane Polymers 0.000 description 2
- 241000567412 Estigmene acrea Species 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 235000001018 Hibiscus sabdariffa Nutrition 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- 235000005291 Rumex acetosa Nutrition 0.000 description 2
- 240000007001 Rumex acetosella Species 0.000 description 2
- 241000256247 Spodoptera exigua Species 0.000 description 2
- 235000003513 sheep sorrel Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 1
- 244000106835 Bindesalat Species 0.000 description 1
- 235000000318 Bindesalat Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- STECJAGHUSJQJN-USLFZFAMSA-N LSM-4015 Chemical compound C1([C@@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-USLFZFAMSA-N 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 240000005407 Nasturtium officinale Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241001674048 Phthiraptera Species 0.000 description 1
- 240000007113 Rumex obtusifolius Species 0.000 description 1
- 235000009422 Rumex obtusifolius Nutrition 0.000 description 1
- 240000001260 Tropaeolum majus Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 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
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/44—Amides thereof
- C07F9/4461—Amides thereof the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4465—Amides thereof the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
RECHTSANWÄLTE
DR-JUCDItI-CHEM-WALTER-BEIl LAWYERS
DR-JUCDItI-CHEM-WALTER-BEIl
ALFRED HOE?P£NOR 8. De2.1972ALFRED HOE? P £ NOR 8. De2.1972
DR. JbR. CiPi.-CC=M. Ji-J. Vv1QLFP l3'*DR. JbR. CiPi.-CC = M. Ji-J. Vv 1 QLFP l3 '*
Dk. JUS. HAf1S CH*. 'ü-liL - Dk. JUS. HAf 1 S CH *. 'ü-liL -
FRAii^rUüi Α,'Λ MAlN~Ht?eHSf FRAii ^ rUüi Α, 'Λ MAlN ~ Ht? EHSf
'■ ADELO.NSliiASSiS»'■ ADELO.NSliiASSiS »
Unsere Nr. 18 377Our no. 18 377
Stauffer Chemical Company Westport, Conn., V. St. A.Stauffer Chemical Company Westport, Conn., V. St. A.
Phosphorsäureimidat-Derivate und dieselben enthaltendle Pestizide - , Phosphoric acid imidate derivatives and pesticides containing the same -,
Die Erfindung betrifft Verbindungen der allgemeinen Formel.The invention relates to compounds of the general formula.
P-N=C-O-R0
■ * R2PN = COR 0
■ * R 2
worin X ein Sauerstoff- oder ein Schwefelatom darstellt) R und R. gleich oder verschieden sein können und jeweils einen niederen Alkylrest mit 1 bis 4 Kohlenstoffatomen, einen niederen Alkoxyrest mit 1 bis 4 Kohlenstoffatomen oder einen niederen Alkylthiorest mit 1 bis 4 Kohlenstoff" atomen bedeuten, wobei, wenn R einen niederen Alkylthiorest darstellt, R. kein niederer Alkylthiorest ist, R-wherein X represents an oxygen or a sulfur atom) R and R. can be the same or different and each a lower alkyl radical with 1 to 4 carbon atoms, a lower alkoxy radical with 1 to 4 carbon atoms or a lower alkylthio radical with 1 to 4 carbon " mean atoms, where, when R represents a lower alkylthio radical, R. is not a lower alkylthio radical, R-
309825/1175309825/1175
ein Wassers toff atom, einen niederen Alkylrest mit 1 bis l Kohlenstoffatomen oder einen Phenylrest und, R- einen gerad- oder verzweißtkettigen niederen Alkylrest mit 1 bis 6 Kohlenstoffatomen bedeuten, und dieselben enthaltende Pestizide, insbesondere Insektizide oder Mitizide.a hydrogen atom, a lower alkyl radical with 1 to 1 carbon atoms or a phenyl radical and, R- denotes a straight or twined-chain lower alkyl radical with 1 to 6 carbon atoms, and pesticides containing the same, in particular insecticides or miticides.
Zur Herstellung der erfindungsgemäßen Verbindungen wirdTo prepare the compounds according to the invention,
saureacid
ein entsprechendes Phosphortimidat in Gegenwart eines alkoholischen Chlorwasserstoffs mit einem entsprechenden Trialkylorthoester umgesetzt. Das Produkt wird in im wesentlichen quantitativen Ausbeuten erhalten und läßt sich von der Reaktionsmasse leicht abtrennen. Nachdem die erfindungsgemüßen Verbindungen hergestellt worden sind, können sie zur Bekämpfungder Insekten in einer wirksamen Menge auf die von Insekten befallene Stelle aufgebracht werden.a corresponding phosphorus imidate in the presence of an alcoholic one Hydrogen chloride with a corresponding trialkyl orthoester implemented. The product is obtained in essentially quantitative yields and can be derived from easily separate the reaction mass. After the inventive Compounds have been made they can be used in an effective amount to control the insects applied to the insect-infested area.
Die nachstehenden Beispiele dienen der Erläuterung der Erfindung.The following examples serve to illustrate the invention.
■." ■ ι
15,Sg (0,10 Mol) S-Äthy1-äthylphosphonamidat, 2U,3 g (0,15■. "■ ι
15, Sg (0.10 mol) S-ethyl-ethylphosphonamidate, 2U, 3 g (0.15
Mol) Trläthylorthoacetat, 0,2 ml alkoholischer Chlorwasserstoff und 50 ml Acetonitril wurden in einem 300 ml-Rundkolben vereinigt. Das Gemisch wurde solange auf einem Dampfbad erhitzt, bis die Temperatur im Kolben 100 C erreichte. Die Reaktionsmasse wurde dann unter Vakuum bei 40 C und 10 μ gestrippt, wobei 22,0 g des gewünschten Produkts er-Mol) Trläthylorthoacetat, 0.2 ml of alcoholic hydrogen chloride and 50 ml of acetonitrile were combined in a 300 ml round bottom flask. The mixture was put on a steam bath heated until the temperature in the flask reached 100C. The reaction mass was then under vacuum at 40 C and 10 μ stripped, with 22.0 g of the desired product
30
halten wurden; ηJ = 1,5945.30th
were holding; ηJ = 1.5945.
Beispiel 2 N-(S-methyl-Q-methylphosphoro)-0-äthylacetimidatExample 2 N- (S-methyl-Q-methylphosphoro) -0-ethylacetimidate
In der gleichen V/eise wie in Beispiel 1 wurden 10 g (0,071 Mol) OjS-Dimethylphosphoramidat, 16,2 g (0,1 Mol) Triäthylorthoacetat, 0,2 ml· alkoholischer Chlorwasserstoff und 50 ml Acetonitril vereinigt, wobei IU,7 g des gewünschten ProduktsIn the same V / eise as in Example 1, 10 g (0.071 mol) of OjS-dimethylphosphoramidate, 16.2 g (0.1 mol) of triethyl orthoacetate, 0.2 ml · alcoholic hydrogen chloride and 50 ml acetonitrile combined to give IU.7 g of the desired product
30
t erhalten wurden; n~ = 1,U677.30th
t were obtained; n ~ = 1, U677.
309825/1175
BAD 309825/1175
BATH
:ί c j π ρ i el 3 ij-(S-Methyl-0-methylphosphoro)-0-äthylformimidat: ί c j π ρ i el 3 ij- (S-methyl-0-methylphosphoro) -0-ethylformimidate
In der gleichen'Weise wie in Beispiel 1 wurden 7,5 g (0,053 Mol) OjS-Dirnethylphosphoramidat, 22,2 g (0,15 Mol) Triäthylorthoformiat, 0,2 ml alkoholischer Chlorwasserstoff und 50 ml Acetonitril vereinigt, wobei 10,4 g des gewünschten ProduktsIn the same way as in Example 1, 7.5 g (0.053 Mol) OjS-dirnethyl phosphoramidate, 22.2 g (0.15 mol) triethyl orthoformate, 0.2 ml of alcoholic hydrogen chloride and 50 ml of acetonitrile are combined to give 10.4 g of the desired product
30
erhalten wurden; η =1,46 80.30th
were obtained; η = 1.46 80.
IR- und NMR-Spektrum bestätigt..IR and NMR spectrum confirmed.
30
erhalten wurden; η =1,46 80. Die Struktur wurde durch30th
were obtained; η = 1.46 80. The structure was through
Beispiel 4 . ■ Example 4 . ■
In der gleichen Weise wie in 'Beispiel 1 wurden 10 g (0,059 Mol) 0,0-Diathylphosphorothxoamidat, 22,2 g (0,15 Mol) Triäthylorthoformidat, 0,2 ml alkoholischer Chlorwasserstoff und 50 ml Acetonitril vereinigt, wobei 131 g des gewünschten Pro-In the same way as in Example 1, 10 g (0.059 Mol) 0,0-diethyl phosphorothxoamidate, 22.2 g (0.15 mol) triethyl orthoformidate, 0.2 ml of alcoholic hydrogen chloride and 50 ml of acetonitrile combined, 131 g of the desired product
30
dukts erhalten wurden; n^ = 1,4497.30th
dukts were obtained; n ^ = 1.4497.
In ähnlicher Weise wurden andere Verbindungen aus den entsprechenden Reagentien hergestellt. In der nachstehenden Tabelle werden typische erfindungsgemäße Verbindungen zusammengestellt. Die den Verbindungen zugeordneten Nummern werden in der weiteren Beschreibung beibehalten.Similarly, other compounds were made from the corresponding Reagents made. Typical compounds according to the invention are compiled in the table below. The numbers assigned to the connections are retained in the further description.
309825/1175309825/1175
BAO ORfOfNALBAO ORfOfNAL
^P-N=C-O-R,^ P-N = C-O-R,
*r i2 * ri 2
VerbinConnect
dung Hr. ;£dung Mr. ; £
10 11 12 13 14 15 16 17 1810 11 12 13 14 15 16 17 18
::
C2H5 C 2 H 5
-OCH-OH
-OCH-OH
-0CH-0CH
-OCH-OH
-OC2H5 -OC2H5 -OC2H5 -OC 2 H 5 -OC 2 H 5 -OC 2 H 5
OC2H5 OC 2 H 5
OC2H5 OC 2 H 5
-OCH3 -OCH 3
-OCH3 -OCH 3
-OCH3 -OCH 3
-OC2Hc-OC 2 Hc
-OCHo-OCHo
-OCH-OH
-SC2H5 -SC 2 H 5
-OC2H5 -OCH,-OC 2 H 5 -OCH,
-SCH-NS
-SCH3 -SCH 3
-OCH3 -OCH 3
-OC2H5 -OC2H5 -SCHo-OC 2 H 5 -OC 2 H 5 -SCHo
-SCH3 -SCH 3
-SCHo-Already
-SC2H5 -SC2II5 -SC2Ii5 -SC 2 H 5 -SC 2 II 5 -SC 2 Ii 5
-SCH-NS
-OCH-OH
-SCH-NS
-SCH-NS
-SCH -CH-SCH -CH
-CH-CH
-C2II-C 2 II
-CH-CH
H
-CH1 H
-CH 1
H
-CH,H
-CH,
H.
-CH,H.
-CH,
.C2H5
H.C 2 H 5
H
-CH3 -CH 3
-C2H5
H- C 2 H 5
H
-C2Il5 "C2H5 -C 2 Il 5 " C 2 H 5
-C2II5 -C 2 II 5
-C2H5 -C 2 H 5
-C2H5 -C 2 H 5
-C2H5 -C 2 H 5
"C2H5 -C2II5 " C 2 H 5 -C 2 II 5
-G2!15 -C2H5 - G 2 ! 1 5 -C 2 H 5
-C2H5 -C2H5 - C 2 H 5 -C 2 H 5
n-C4Hg -CH,nC 4 H g -CH,
-CH-CH
309825/ 1309825/1
I. Stubenfliege (Musca domestica (L.) (HF) Filmrückstand ·I. House fly (Musca domestica (L.) (HF) Film residue
Es wurde eine Vorratslösung mit einem Gehalt von 100 ug/ml' des Giftstoffes in einem geeigneten Lösungsmittel herge-' stellt. Aliquote Teile dieser Lösung wurden mit 1 ml einer Aceton-Erdnußöl-Lösung in einer Schale mit einem Durchmesser von 55 mm vereinigt und trocknen gelassen. Die aliquoten Teile wurden so variiert, daß man die gewünschten Konzentrationen an Giftstoff im Bereich von 100 fig pro Schale bis zu der Konzentration, bei der eine 50 %igeSterblichkeit erreicht wurde, erhielt. Die Schalen wurden in einen kreisrunden P&ppkafig gestellt, der am Boden mit Cellophan verschlossen und oben mit einem Stoffnetζ bedeckt war. 25 weibliche Stubenfliegen, wurden in den Käfig gebracht, und nach HS Stunden wurde die prozentuale Sterblichkeit festgestellt. Die LD^-Werte sind in Mg pro 25 weibliche Fliegen wiedergegeben.A stock solution containing 100 ug / ml ' of the poison in a suitable solvent. Aliquots of this solution were mixed with 1 ml of a Acetone-peanut oil solution combined in a dish with a diameter of 55 mm and allowed to dry. The aliquots Portions were varied so that you get the desired concentrations of toxin in the range of 100 fig per Peel up to the concentration at which there is a 50% mortality was achieved, received. The dishes were placed in a circular P & pp cage that was placed on the bottom with Sealed with cellophane and covered with a cloth net on top was. 25 female houseflies were in the cage brought, and after HS hours, the percent mortality was determined established. The LD ^ values are in Mg per 25 reproduced female flies.
II. Deutsche Küchenschabe (Blattella germanica (Linne) (GR)II. German cockroach (Blattella germanica (Linne) (GR)
10 einen Monat alte Nymphen wurden in einen kreisrunden Pappkafig gebracht, der auf der einen Seite mit Cellophan verschlossen und auf der anderen mit einem Stoffnetz bedeckt war. Aliquote Teile des Giftstoffes, gelöst in einem geeigneten Lösungsmittel, wurden mit Wasser verdünnt, dem 0,0002 % eines herkömmlichen Netzmittels, wie z. B. PoIyoxyäthylensorbitanmonolauratäther von alkylierten Phenolen, vermischt mit organischen Sulfonaten, zugesetzt waren. Die Testkonzentrationen reichten von 0,1 % bis herab zu derjenigen Konzentration, bei der eine 50 %ige Sterblichkeit er- · reicht wurde. Jede dieser wäßrigen Suspensionen wurde durch das Stoffnetz mittels einer Handsprühpistole auf die Insekten gesprüht. Die prozentuale Sterblichkeit wurde nach 72.Stunden registriert, und die LD5Q-Werte wurden als Prozentgehalt des Giftstoffes in dem wäßrigen Spray ausgedrückt Ten one-month-old nymphs were placed in a circular cardboard cage, which was closed with cellophane on one side and covered with a cloth net on the other. Aliquots of the toxin, dissolved in a suitable solvent, were diluted with water containing 0.0002% of a conventional wetting agent such as e.g. B. Polyoxyäthylensorbitanmonolauratäther of alkylated phenols, mixed with organic sulfonates, were added. The test concentrations ranged from 0.1% down to the concentration at which a 50% mortality was achieved. Each of these aqueous suspensions was sprayed onto the insects through the cloth net using a hand spray gun. The percent mortality was recorded after 72 hours and the LD 5Q values were expressed as the percentage of the toxin in the aqueous spray
309 825/1175309 825/1175
TII. i»yf,ur,-VJanze ( Lygur; hesperuo {Knight)) (LB)TII. i »yf, ur, -VJanze (Lygur; hesperuo {Knight)) (LB)
VUc btii der deutschen Küchenschabe (II), jedoch mit der Ausii.ιίιΐ,.e , daß die Tostkonzentrationen von 0,05 % bis zu der Konzentration reichten, bei der eine 50 %ige Sterblichkeit erzielt wurde.VUc btii of the German cockroach (II), but with the Ausii.ιίιΐ, .e that the toast concentrations ranged from 0.05% to the concentration at which a 50% mortality was achieved.
IV. Schwarze Bohnenblattlaus (Aphis fabae (Scop.) (BA)IV.Black bean aphid (Aphis fabae (Scop.) (BA)
Brunnenkresse-Pflanzen (Nasturtium Tropaeolum sp.) mit einer Größe von etwa 5 bis 8 cm wurden in sandigen Lehmboden in 8 cm große Tontöpfe gepflanzt und mit 50-75 Läusen unterschiedlichen Alters besetzt. Mach 24 Stunden wurden sie bis zum Abtropfen mit wäßrigen Suspensionen des Giftstoffs besprüht. Die Suspensionen wurden wie in den vorstehend beschriebenen Versuchen (I, II und III) hergestellt. Die Testkonzentrationen reichten von 0,05 % bis zu der Konzentration, bei der eine 50 %ige Sterblichkeit erreicht wurde. Die Sterblichkeit wurde nach 48 Stunden festgestellt, und die LD,~- Werte wurden als Prozentgehalt des Wirkstoffs in den wäßrigen Suspensionen ausgedrückt.Watercress plants (Nasturtium tropaeolum sp.) With a Size of about 5 to 8 cm were planted in sandy loam soil in 8 cm clay pots and with 50-75 different lice Age occupied. After 24 hours they were sprayed with aqueous suspensions of the toxin until they drained off. The suspensions were prepared as in experiments (I, II and III) described above. The test concentrations ranged from 0.05% to the concentration at which 50% mortality was reached. The mortality was found after 48 hours, and the LD, ~ - Values were expressed as the percentage of the active ingredient in the aqueous suspensions.
V. Salzsumpf-Raupe (Estigmene acrea (Drury)) (SMC)V. Salt marsh caterpillar (Estigmene acrea (Drury)) (SMC)
Testlösungen wurden in gleicher Weise und in denselben Konzentrationen wie für die deutsche Küchenschabe (II) zubereitet. Stücke von Sauerampferblättern (Rumex obtusifolius) von 2,5 bis 4 cm Länge wurden 10 bis 15 Sekunden lang in die Testlösungen getaucht und zum Trocknen auf ein Drahtnetz gelegt. Das getrocknete Blatt wurde auf ein angefeuchtetes Stück Filterpapier in einer Petrischale gelegt und mit fünf Larven im 3. Instar-Stadium (third-instar larvae) besetzt. Die Sterblichkeit der Larven wurde nach 72 Stunden registriert, und die LD,.Q-Werte wurden als Prozentgehalt des Wirkstoffs in den wäßrigen Suspensionen ausgedrückt.Test solutions were made in the same way and in the same concentrations as prepared for the German cockroach (II). Pieces of sorrel leaves (Rumex obtusifolius) 2.5 to 4 cm in length were immersed in the test solutions for 10 to 15 seconds and placed on a wire mesh to dry. The dried sheet was placed on a moistened piece of filter paper in a petri dish and with five Larvae in the 3rd instar stage (third-instar larvae) occupied. Larval mortality was recorded after 72 hours and the LD, .Q values were expressed as a percentage of the Active ingredient expressed in the aqueous suspensions.
VI. Rüben-Heerwurm (Spodoptera exigua (Hübner)) (BAV/)VI. Beet Army Worm (Spodoptera exigua (Huebner)) (BAV /)
Wie bei der Saizsumpf-Raupe (V), jedoch mit der Ausnahme, daß anstelle* von Sauerampfer Blätter von Römischem Salat (Latuca sativa) als Wirtspflanze verwandt wurden.As with the Saizsumpf caterpillar (V), but with the exception that instead of * sorrel leaves of romaine lettuce (Latuca sativa) were used as the host plant.
3 0 9 8 2 5/11753 0 9 8 2 5/1175
clu:»j, Ur. Connecting
clu "j, Ur.
ir,17th
ir,
503
50
GR LB - BA SMC BAUGR LB - BA SMC CONSTRUCTION
■0,03 0,005 0r008■ 0.03 0.005 0 r 008
■0,1 0,03 >0,05■ 0.1 0.03> 0.05
O?.O8 >0,05 >0,05O ? .O8>0.05> 0.05
O1OS 0,008 0f008 >0,l 0r03O 1 OS 0.008 0 f 008> 0, l 0 r 03
0,03 0^008 0,003 >Ό,1 0,010.03 0 ^ 008 0.003 > Ό, 1 0.01
0,03 0,01 0,008 >0,l 0; 080.03 0.01 0.008> 0.1 0 ; 08
>0,05 >0,l >0,05 . ; >0,l·> 0.05> 0.1 l> 0.05. ; > 0, l
0,03 0,008 0,003 >O,1 '■ 0,030.03 0.008 0.003 > 0.1 '■ 0.03
0,05 0,03 0,03 0,1 0.080.05 0.03 0.03 0.1 0.08
0,05 0,01 ■ 0,005 >0,l 0?030.05 0.01 ■ 0.005> 0, l 0 ? 03
0,1 0,01 °7O3 > 0,1 0,10.1 0.01 ° 7 O3> 0.1 0.1
OjI 0,05 0,03 ■ >0,l >0,lOjI 0.05 0.03 ■> 0.1 > 0, l
■0,1 >0 7O5 0,03 >0,l >0;l■ 0.1> 0 7 O5 0.03> 0, l>0; l
0;01 0?03 0,008 >0,l 0,030 ; 01 0 ? 03 0.008> 0.1 l 0.03
0;01 0 ,03 0,03 > 0,1 0;030 ; 01 0.03 0.03> 0.1 0 ; 03
0,003 0,03 0,003 0,08 0,010.003 0.03 0.003 0.08 0.01
0?08 >0 ,05 0t03- >0,1 >0;ΐ0 ? 08> 0.05 0 t 03->0.1> 0 ; ΐ
3 0 9 8 2 5/11753 0 9 8 2 5/1175
Claims (20)
P-N=C-O-R X
PN = COR
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20758771A | 1971-12-13 | 1971-12-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2260576A1 true DE2260576A1 (en) | 1973-06-20 |
Family
ID=22771193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2260576A Pending DE2260576A1 (en) | 1971-12-13 | 1972-12-11 | PHOSPHORIC ACID IMIDATE DERIVATIVES AND PESTICIDES CONTAINING THE SAME |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS4867437A (en) |
| AR (1) | AR195689A1 (en) |
| AU (1) | AU4978972A (en) |
| BE (1) | BE792671A (en) |
| BR (1) | BR7208794D0 (en) |
| DE (1) | DE2260576A1 (en) |
| FR (1) | FR2163543B1 (en) |
| GB (1) | GB1373893A (en) |
| IL (1) | IL41113A0 (en) |
| IT (1) | IT971803B (en) |
| NL (1) | NL7216916A (en) |
| ZA (1) | ZA728802B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0204949A1 (en) * | 1985-05-14 | 1986-12-17 | Nihon Tokushu Noyaku Seizo K.K. | Phosphoroimidates |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01233202A (en) * | 1988-03-11 | 1989-09-19 | Sumitomo Chem Co Ltd | Stabilization of thiophosphoric acid ester and stable agricultural chemical composition containing said ester as active component |
-
0
- BE BE792671D patent/BE792671A/en unknown
-
1972
- 1972-12-07 AU AU49789/72A patent/AU4978972A/en not_active Expired
- 1972-12-11 DE DE2260576A patent/DE2260576A1/en active Pending
- 1972-12-12 FR FR7244224A patent/FR2163543B1/fr not_active Expired
- 1972-12-12 AR AR245593A patent/AR195689A1/en active
- 1972-12-12 GB GB5688472A patent/GB1373893A/en not_active Expired
- 1972-12-13 IT IT32834/72A patent/IT971803B/en active
- 1972-12-13 ZA ZA728802A patent/ZA728802B/en unknown
- 1972-12-13 NL NL7216916A patent/NL7216916A/xx unknown
- 1972-12-13 JP JP47124441A patent/JPS4867437A/ja active Pending
- 1972-12-13 BR BR008794/72A patent/BR7208794D0/en unknown
- 1972-12-18 IL IL41113A patent/IL41113A0/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0204949A1 (en) * | 1985-05-14 | 1986-12-17 | Nihon Tokushu Noyaku Seizo K.K. | Phosphoroimidates |
| US4692436A (en) * | 1985-05-14 | 1987-09-08 | Nihon Tokushu Noyaku Seizo K.K. | Phosphoroimidates as pesticides |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4867437A (en) | 1973-09-14 |
| ZA728802B (en) | 1973-09-26 |
| FR2163543B1 (en) | 1976-08-20 |
| BE792671A (en) | 1973-06-13 |
| IT971803B (en) | 1974-05-10 |
| GB1373893A (en) | 1974-11-13 |
| AR195689A1 (en) | 1973-10-31 |
| NL7216916A (en) | 1973-06-15 |
| FR2163543A1 (en) | 1973-07-27 |
| IL41113A0 (en) | 1973-02-28 |
| BR7208794D0 (en) | 1973-08-30 |
| AU4978972A (en) | 1974-06-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2052379B2 (en) | 0- (N-Alkoxy-benzimidoylHthiono) phosphor (phosphonic) acid ester, process for their preparation and their use as insecticides and acaricides | |
| EP0100528A2 (en) | Derivatives of (di)-thiophosphoric and (di)-thiophosphonic acids, process for their preparation, compositions containing them and their use in plant protection | |
| DE2462422A1 (en) | 2-CARBAMOYLOXIMINO-1,4-OXATHIACYCLOHEXANE AND THEIR 4-OXIDES AND 4,4-DIOXIDES AND METHOD FOR THEIR PRODUCTION | |
| DE2260576A1 (en) | PHOSPHORIC ACID IMIDATE DERIVATIVES AND PESTICIDES CONTAINING THE SAME | |
| DE2732930C2 (en) | New 0-ethyl-S-n-propyl-O-2,2,2-trihalogenäthylphosphorthiolate (or -thionothiolate), process for their preparation and their use as insecticides, acaricides and nematicides | |
| DE3118257A1 (en) | PESTICIDES S (-1.2.4-TRIAZOL-5-YLMETHYL) - (DI) -THIOPHOSPH (ON) ATE AND METHOD FOR THE PRODUCTION THEREOF | |
| DE2163392C3 (en) | New phosphoric acid esters and processes for their production | |
| US4194029A (en) | Novel 4-chromanone-7-phosphates and phosphonates and the insecticidal use thereof | |
| DE2232076A1 (en) | ORGANIC PHOSPHORIC ACID ESTERS, PROCESS FOR THEIR PRODUCTION AND THEIR USE AS INSECTICIDES, ACARICIDES AND NEMATOCIDES | |
| DE1768399A1 (en) | O-alkyl-O-aryl-thiolphosphoric acid ester | |
| DE2246759A1 (en) | NEW SUBSTITUTED TRITHIOPHOSPHONATES AND THEIR USE AS INSECTICIDES | |
| US3947481A (en) | Organotin miticidal and insecticidal compounds | |
| CH627620A5 (en) | Method and composition for controlling insects and acarids | |
| US3642958A (en) | Isobutoxy-s-(4-chlorophenyl) ethylphosphonodithioate | |
| US4036958A (en) | Insecticidal and miticidal active isothiuronium tricyclohexyl tin imide | |
| DE2034478C3 (en) | O-alkyl-O-phenyl-S-alkoxyethylphosphorothiolate with insecticidal and fungicidal action | |
| US3351680A (en) | Omicron, omicron-diloweralkyl phosphorodithioyl-methyl-substituted mercaptoacetates | |
| DE2243612A1 (en) | THIOPHEN-GLYOXYLONITRIL-OXIM-PHOSPHORIC ACID DERIVATIVES AND THEIR USES | |
| DE1935758C (en) | (Thio) phosphonic acid esters and their use as active ingredients in pesticides | |
| AT362197B (en) | METHOD FOR CONTROLLING INSECTS, MITES, AND NEMATODES | |
| CH532083A (en) | Process for the production of new amidothionophosphoric acid phenyl esters, and their use for the production of insecticidal and acaricidal agents | |
| DE1668047C (en) | Amidothionophosphoric acid phenyl ester, their preparation and insecticidal and acaricidal agents | |
| US4044025A (en) | Organotin miticidal and insecticidal compounds | |
| DE1668012C3 (en) | Process for the preparation of thiol or thionothiolphosphoric acid esters, thionothiolphosphoric acid esters and insecticidal, acaricidal and nematocidal agents containing them | |
| DE2704894A1 (en) | NEW FORMAMIDINO-DITHIOPHOSPHATES AND -PHOSPHONATES AND THEIR USE AS INSECTICIDES |