IL33504A - The production of esters and amides of o-(-2-bromoethyl)-o-(2,2-dichlorovinyl)-phosphoric acid,and pesticidal compositions containing such compounds - Google Patents
The production of esters and amides of o-(-2-bromoethyl)-o-(2,2-dichlorovinyl)-phosphoric acid,and pesticidal compositions containing such compoundsInfo
- Publication number
- IL33504A IL33504A IL33504A IL3350469A IL33504A IL 33504 A IL33504 A IL 33504A IL 33504 A IL33504 A IL 33504A IL 3350469 A IL3350469 A IL 3350469A IL 33504 A IL33504 A IL 33504A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- carbon atoms
- formula
- alkyl
- admixture
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 40
- 150000002148 esters Chemical class 0.000 title claims description 8
- 239000000203 mixture Substances 0.000 title claims description 8
- 150000001408 amides Chemical class 0.000 title claims description 5
- 230000000361 pesticidal effect Effects 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 title 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 9
- 239000003085 diluting agent Substances 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 241000607479 Yersinia pestis Species 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- VHCWNORMONAZKG-UHFFFAOYSA-N 2-bromo-2,2-dichloroacetaldehyde Chemical compound ClC(Cl)(Br)C=O VHCWNORMONAZKG-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 3
- -1 dialkenylamino Chemical group 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 101100324525 Rattus norvegicus Asrgl1 gene Proteins 0.000 claims 1
- 125000004947 alkyl aryl amino group Chemical group 0.000 claims 1
- 125000005248 alkyl aryloxy group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000004986 diarylamino group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 241001465754 Metazoa Species 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 238000003197 gene knockdown Methods 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 2
- 241000256118 Aedes aegypti Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- MHZDONKZSXBOGL-UHFFFAOYSA-N propyl dihydrogen phosphate Chemical compound CCCOP(O)(O)=O MHZDONKZSXBOGL-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007858 starting material 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657154—Cyclic esteramides of oxyacids of phosphorus
-
- 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
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/113—Esters of phosphoric acids with unsaturated acyclic alcohols
-
- 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
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/173—Esters of thiophosphoric acids with unsaturated acyclic alcohols
-
- 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
- C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2412—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of unsaturated acyclic alcohols
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
The present invention relates to an unobvious process for the production of insecticidal acid esters or and to some of these pounds which are Prom German Patent Specification it is known that dioxaphospholanes can be reacted with chloral to give acid in German Published Specification 1 232 961 there is already described a process for the preparation of esters of some acids of phosphorus which among other things but in a completely different way to acid It has now been found that the analogously structured bromoethy acid compounds of the general formula R 0 i in which R stands for alkoxyalkyl or and X stands for dialkylamino alkylarylamino or can be prepared in high yield and purity by a process in which of the general formula ο t In this connection it is most surprising and unexpected that only the bromine atom causes the splitting of the pholane ring and enters the newly formed Since as stated in the German patent specification mentioned brings about the ring splitting described with the same ease in exothermal it was to have been expected that the use of bromodichloroacetaldehyde instead of chloral would give a mixed product in which bromine and chlorine atoms are distributed stically between the haloalkyl and the dihalovinyl is not the The products of the process according to the invention are homogeneous and correspond to the general formula as can be proved for example by nuclear resonance the process according to the measured against the prior represents an If and dehyde are used as starting the reaction can be esented by the following reaction The to be used as starting materials are generally defined by the above formula In formulae and it is preferred that stands for alkyl or haloalkyl with carbon alkoxyalkyl with carbon or alkenoxyalkyl with 3 to 6 carbon and X for alkoxy or with carbon lower As examples of the of formula which can be used according to the the following may be hospholane thio allyloxy The compounds of formula are known and can be produced even on an industrial The reaction may be carried out in the presence of a 5 such as benzene and ohlorlnated aliphatic such as and and suoh as diethyl In the reaction be carried out without a The reaction temperatures can be varied within a fairly wide In the work is carried out at from 0 to preferably 30 to The reaction is and temperature oan be regulated by addition of the aldehyde of the formula For the carrying out of the process aocording to the the desired of the formula may be dissolved in one of the solvents mentioned and the amount of of the formula may be added For working the reaotion solutions are washed dried and Many of the products so obtained can be purified by Where this is not possible because of the risk of the crude products may be under greatly reduoed from residues of The substanoes obtainable according to the process of the invention for the most and are used as The invention also provides a pesticidal composition ontaining as active ingredient a compound produced by a process according to the invention in admixture with a liquid diluent or carrier containing a active The diluent or carrier may be any of those known to the The composition generally contains to 90 by weight of the and may be diluted for actual The invention also provides a method of combating Le A 11931 5a cultural peata which comprisee to the peats or a habitat thereof a compound according to the invention or produced by a process according to the invention alone or in the form of a composition containing as aotive ingredient the compound in mixture with a solid or liquid diluent or The invention also provides crops protected from damage by pests by being grown in areas in prior to or during the time of the a compound according to the invention or produced by a process according to the invention was applied alone or in admixture with a solid or liquid diluent or The process of the and the pesticidal activity of the are illustrated by the following Example 1 0 48 g 25 are added with to 5 g pholane in 200 ml The temperature rises to Stirring is continued for two to three the temperature falling again to room The reaction mixture is washed neutral with dried over sodium filtered off and For the oily residue can be obtained as colourless oil of boiling point Hg and the refractive index g of the Calculated for 9 Example 2 0 The compound is prepared analogously to that of Example 1 from pro and propyl phosphoric acid ester is obtained as a colourless oil of boiling point mm Hg and the refractive index of the theory Calculated for Example 3 The compound is prepared analogously to Example 1 from and acid ester is obtained as yellow oil of boiling point 3 mm Hg and the refractive index Yield of the theory Analysis P S Calculated for Example 4 0 The compound is prepared analogously to Example 1 from and h l l Hg and refractive index of the theory Calculated for The compound is prepared analogously to Example 1 from and acid amide is obtained as colourless oil of boiling point mm Hg and the refractive index of the theory N P Calculated for Example 6 Q The compound is prepared analogously to Example 1 from and acid amide is obtained as colourless oil of boiling point mm Hg and the refractive index of the theory N P Calculated for Example 7 The compound prepared analogously to Example 1 from and acid ester is obtained as yellowish oil of boiling point mm Hg and the tive index of the Calculated for Example 8 The compound is prepared analogously to Example 1 from and but stirring is effected at 50 to acid ester is obtained oil of refractive index of the theory Analysi Calculated for Example 9 The prepared analogously to Example 1 from and acid eater is obtained as yellow oil of 21 refractive index of the theory Calculated for Example The compound is prepared analogously to Example 1 from and acid ester is obtained as yellow oil of refractive index of the theory Calculated for Le A 10 Example A Teat Aedes aegypti Solven Acetone 2 parts by weight of active compound are dissolved in 1000 parts by volume of The solution so obtained is diluted with further solvent to the desired lower ml of the solution of active compound are pipetted into a Petri On the bottom of the Petri dish there is a filter paper with a diameter of about The Petri dish remains uncovered until the solvent has completely The amount of active compound per square metre of filter paper varies with the concentration of the solution of active compound About 25 test animals are then placed in the Petri dish and it is covered with a glass The condition of the test animals is continuously The time which is necessary for a knock down effect is The test the active the concentrations of the active compounds and the periods of time at which there is a knock down effect can be from Table Table A Active compounds Concentrations of active compound solution 0 2 5 A 11931 12 Example B Test domestiea Solven Acetone 2 parte by weight of active compound are dissolved in 1000 parts by volume of The solution so obtained is diluted with further solvent to the desired lower ml of the solution of active compound are pipetted into a Petri On the bottom of the Petri dish there is a ter paper with a diameter of about The Petri dish remains uncovered until the solvent has completely The amount of active compound per square metre of filter paper varies with the concentration of the solution of active compound About 25 test animals are then placed in the Petri dish and it is covered with a glass The condition of the test animals is continuously The time which is necessary for a knock down effect is The test the active the concentrations of the active compounds and the periods of time at whioh there is a knock down effect can be seen from Table Table B for Dlptera Ac ive compounds Concentrations of active compound solution Example G Teat animals Sitophilua granarius Solven Acetone 2 parts by weight of the active compound are dissolved in 1000 parts by volume of the The solution so obtained is diluted with further solvent to the desired concentrations ml of the solution of the active compound are pipetted into a Petri On the bottom of the Petri dish there is a filter paper with a diameter of about The Petri dish mains uncovered until the solvent has completely The amount of active compound per square metre of filter paper varies with the concentration of the solution of active compound About 25 test animals are then placed in the Petri dish and it is oovered with a glass The condition of the test animals is observed after 1 and 3 days after the commencement of the The knock down effect is determined as a The active the concentratio s of the active the test animals and the results can be seen from Table Table AotiTe compounda Concentrations of Destruction compound in 0 100 30 insufficientOCRQuality
Claims (15)
1. A prooess for the production of a 2- acid ester or amide of the formula H 0 Br-CH2-CH-0-P-0-CH=0Cl2 (I ) X in which H stands for hydrogen, alkyl, haloalkyl, alkoxyalkyl or alkenoxyalkyl, and .thio X stands for alkoxy, aryloxy, alkylaryloxy, alkylAercapto , .thio arylaegeapte, dialkylamino, dialkenylamino, diarylamino, alkylarylamino or T-alkyl-2-alkoxycarbonyl7-vinyloxy in which a 1, 3»2-dioxaphospholane of the general formula is reacted with bromodichloroacetaldehyde of the formula CI 0 Br-C- C (III) t I CI H
2. A process according to claim 1 in which R stands for alkyl or haloalkyl with 1-4 carbon atoms, alkoxyalk l with 2-6 carbon atoms, or alkenoxyalkyl with 3 to 6 carbon atoms; and X for alkoxy or alkylaeseep-*©- with 1-4 carbon atoms, £L-methyl-2-ethoxycarbonyl /thio -vinyl-oxy, phenoxy, lower alkylphenyloxy, phenylmei-aap e^ dialkylamino with 2-8 carbon atoms, dialkenylamino with 4-8 carbon atoms, diphenylamino, or N-alkyl-N-arylamino, especially N-lower-alkyl-N-phenylamino.
3. A process according to claim 1 or 2 in which the compound of formula (II) is one of those hereinbefore listed.
A rooess aooordin to an of claims 1-3 in which the reac 33504/2 - 18 -
5. A process aocording to claim 4 in hiob the solvent is one of those hereinbefore mentioned.
6. -A prooeas acoording to any of. olaima 1-5 in hioh the reaction ia carried out at 0 to 100°C.
7. A prooesa according to claim 6 in whioh the reaotion ia oarried out at 30 to 70°C.
8. A prooesa acoording to any of claims 1-7 in whioh the compound of the formula (II) ia dissolved in a solvent and an equimolar amount of bromodiohloroacetaldehyde ia added dropwiae.
9. A prooeas aocording to olaim 1, substantially as hereinbefore described in any of Examples 1-10.
10. 0- 2-bromoethy3 -0-^,2-diohlorovinyl7-pbosphorio acid eaters and amides as defined in olaim 1, whenever prepared by a process acoording to any of claims 1-9.
11. Gompounds hereinbefore identified as (4), (9) and (10) whenever prepared by a process according to any of Claims 1-9.
12. A pesticidal composition containing as active ingredient a compound according to Claim 10 or 11 in admixture with a solid diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent.
13. A composition a ccording to Claim 12 containing from 0.1 to 5$ of the active compound by weight.
14. A method of combating agricultural pests which comprises applying to the pests or a habitnt thereof a compoind according to Claim 10 or 11 alone or in the form of a composition containing as active ingredient a compound according to Claim 10 or 11 in admixture with a solid or liquid diluent or carrier. 33504/2 19
15. Crops protected from daaaage by being grown in areas in which, imnediately prior to and/or during the time of the growing, a compound according to any of Claims 10 or 11 was applied alone or in admixture with a solid or liquid diluent or carrier. ND:BH
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1816903A DE1816903C3 (en) | 1968-12-24 | 1968-12-24 | 0- [2-bromoethyl] - 0 - [2,2-dichloro-vinyl] phosphoric acid ester !! or amides, process for their production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL33504A0 IL33504A0 (en) | 1970-02-19 |
| IL33504A true IL33504A (en) | 1972-12-29 |
Family
ID=5717339
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL33504A IL33504A (en) | 1968-12-24 | 1969-12-09 | The production of esters and amides of o-(-2-bromoethyl)-o-(2,2-dichlorovinyl)-phosphoric acid,and pesticidal compositions containing such compounds |
Country Status (14)
| Country | Link |
|---|---|
| AT (1) | AT291296B (en) |
| BE (1) | BE743707A (en) |
| BG (1) | BG17012A3 (en) |
| CH (1) | CH533641A (en) |
| CS (1) | CS158659B2 (en) |
| DE (1) | DE1816903C3 (en) |
| DK (1) | DK122967B (en) |
| ES (1) | ES374846A1 (en) |
| FR (1) | FR2027083A1 (en) |
| GB (1) | GB1243599A (en) |
| IL (1) | IL33504A (en) |
| NL (1) | NL6919029A (en) |
| RO (1) | RO56628A (en) |
| YU (1) | YU316069A (en) |
-
1968
- 1968-12-24 DE DE1816903A patent/DE1816903C3/en not_active Expired
-
1969
- 1969-12-08 CH CH1823269A patent/CH533641A/en not_active IP Right Cessation
- 1969-12-09 IL IL33504A patent/IL33504A/en unknown
- 1969-12-15 DK DK662969AA patent/DK122967B/en unknown
- 1969-12-16 BG BG013558A patent/BG17012A3/en unknown
- 1969-12-17 RO RO61896A patent/RO56628A/ro unknown
- 1969-12-17 YU YU03160/69A patent/YU316069A/en unknown
- 1969-12-18 NL NL6919029A patent/NL6919029A/xx not_active Application Discontinuation
- 1969-12-22 CS CS844669A patent/CS158659B2/cs unknown
- 1969-12-23 GB GB62581/69A patent/GB1243599A/en not_active Expired
- 1969-12-23 ES ES374846A patent/ES374846A1/en not_active Expired
- 1969-12-23 AT AT1198869A patent/AT291296B/en not_active IP Right Cessation
- 1969-12-24 BE BE743707D patent/BE743707A/xx unknown
- 1969-12-24 FR FR6944996A patent/FR2027083A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| DK122967B (en) | 1972-05-01 |
| CH533641A (en) | 1973-02-15 |
| FR2027083A1 (en) | 1970-09-25 |
| AT291296B (en) | 1971-07-12 |
| DE1816903B2 (en) | 1977-09-22 |
| ES374846A1 (en) | 1972-01-16 |
| BE743707A (en) | 1970-06-24 |
| RO56628A (en) | 1974-09-01 |
| CS158659B2 (en) | 1974-11-25 |
| NL6919029A (en) | 1970-06-26 |
| GB1243599A (en) | 1971-08-18 |
| YU316069A (en) | 1978-10-31 |
| DE1816903C3 (en) | 1978-05-24 |
| BG17012A3 (en) | 1973-04-25 |
| DE1816903A1 (en) | 1970-07-16 |
| IL33504A0 (en) | 1970-02-19 |
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