CS216224B2 - Insecticide and acaricide means and method of making the synergically active substance - Google Patents
Insecticide and acaricide means and method of making the synergically active substance Download PDFInfo
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- CS216224B2 CS216224B2 CS806022A CS602280A CS216224B2 CS 216224 B2 CS216224 B2 CS 216224B2 CS 806022 A CS806022 A CS 806022A CS 602280 A CS602280 A CS 602280A CS 216224 B2 CS216224 B2 CS 216224B2
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- Czechoslovakia
- Prior art keywords
- acid
- spec
- carbon atoms
- propargyl
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- 230000000895 acaricidal effect Effects 0.000 title claims description 5
- 239000013543 active substance Substances 0.000 title description 20
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000002917 insecticide Substances 0.000 title description 2
- 239000000642 acaricide Substances 0.000 title 1
- 239000002253 acid Substances 0.000 claims abstract description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 15
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 12
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 9
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 claims abstract description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
- UTTHRBIOOHIUBW-UHFFFAOYSA-N methyl(prop-2-ynoxy)phosphinic acid Chemical class CP(O)(=O)OCC#C UTTHRBIOOHIUBW-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000001301 oxygen Substances 0.000 claims abstract description 7
- 239000011230 binding agent Substances 0.000 claims abstract description 5
- 150000007529 inorganic bases Chemical class 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 11
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 11
- 229910052717 sulfur Chemical group 0.000 claims description 10
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 9
- 239000011593 sulfur Chemical group 0.000 claims description 8
- 150000001350 alkyl halides Chemical class 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 claims description 4
- 230000000749 insecticidal effect Effects 0.000 claims description 4
- 150000004714 phosphonium salts Chemical class 0.000 claims description 4
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- 239000011574 phosphorus Substances 0.000 claims description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 1
- -1 alkinyl radical Chemical class 0.000 abstract description 41
- 125000000217 alkyl group Chemical group 0.000 abstract description 25
- 150000002148 esters Chemical class 0.000 abstract description 13
- 238000002360 preparation method Methods 0.000 abstract description 10
- 239000005864 Sulphur Substances 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 description 14
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- 239000000126 substance Substances 0.000 description 10
- 230000002195 synergetic effect Effects 0.000 description 10
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- 125000003118 aryl group Chemical group 0.000 description 8
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- 238000000199 molecular distillation Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- ZWRDBWDXRLPESY-UHFFFAOYSA-N n-benzyl-n-ethylethanamine Chemical compound CCN(CC)CC1=CC=CC=C1 ZWRDBWDXRLPESY-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000002270 phosphoric acid ester group Chemical group 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- SBUAYSSKTAGAGF-UHFFFAOYSA-N prop-2-ynyl dihydrogen phosphate Chemical class OP(O)(=O)OCC#C SBUAYSSKTAGAGF-UHFFFAOYSA-N 0.000 description 1
- DPTIIEGNOZAWAW-UHFFFAOYSA-N prop-2-ynylphosphonic acid Chemical compound OP(O)(=O)CC#C DPTIIEGNOZAWAW-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000010453 quartz 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
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000004963 sulfonylalkyl group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- CEYYIKYYFSTQRU-UHFFFAOYSA-M trimethyl(tetradecyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)C CEYYIKYYFSTQRU-UHFFFAOYSA-M 0.000 description 1
- ADZJWYULTMTLQZ-UHFFFAOYSA-N tritylphosphane;hydrobromide Chemical compound [Br-].C=1C=CC=CC=1C(C=1C=CC=CC=1)([PH3+])C1=CC=CC=C1 ADZJWYULTMTLQZ-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 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
- C07F9/28—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)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4078—Esters with unsaturated acyclic alcohols
-
- 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
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
-
- 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
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing aromatic radicals
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Lubricants (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792936037 DE2936037A1 (de) | 1979-09-06 | 1979-09-06 | Propargylgruppenhaltige methanphosphonsaeureester und deren verwendung in synergistischen wirkstoffkombinationen zur schaedlingsbekaempfung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS216224B2 true CS216224B2 (en) | 1982-10-29 |
Family
ID=6080212
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS806022A CS216224B2 (en) | 1979-09-06 | 1980-09-04 | Insecticide and acaricide means and method of making the synergically active substance |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP0025179B1 (xx) |
| JP (1) | JPS5640692A (xx) |
| AT (1) | ATE2598T1 (xx) |
| AU (1) | AU6198480A (xx) |
| BR (1) | BR8005659A (xx) |
| CS (1) | CS216224B2 (xx) |
| DD (1) | DD152715A5 (xx) |
| DE (2) | DE2936037A1 (xx) |
| DK (1) | DK379680A (xx) |
| IL (1) | IL60956A0 (xx) |
| PL (1) | PL226601A1 (xx) |
| PT (1) | PT71743B (xx) |
| SU (1) | SU982527A3 (xx) |
| TR (1) | TR20814A (xx) |
| ZA (1) | ZA805504B (xx) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0211924D0 (en) * | 2002-05-23 | 2002-07-03 | Syngenta Ltd | Composition |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3065125A (en) * | 1960-01-28 | 1962-11-20 | Monsanto Chemicals | Alkynyl phosphonothioates |
| US3860711A (en) * | 1970-04-30 | 1975-01-14 | Johnson & Son Inc S C | Synergistic insecticidal composition containing dipropargyl phenylphosphonate |
| US3856896A (en) * | 1973-02-09 | 1974-12-24 | Johnson & Son Inc S C | Alkyl propargyl phosphonates |
| IL48428A0 (en) * | 1974-11-15 | 1976-03-31 | Fmc Corp | Synergistic insecticidal compositions containing a cyclopropane carboxylate and a phosphonate |
| DE2727479A1 (de) * | 1977-06-18 | 1979-01-04 | Bayer Ag | Insektizide und akarizide mittel |
| DE2853450A1 (de) * | 1978-12-11 | 1980-06-19 | Basf Ag | Thionophosphonsaeureester |
-
1979
- 1979-09-06 DE DE19792936037 patent/DE2936037A1/de not_active Withdrawn
-
1980
- 1980-08-27 EP EP80105075A patent/EP0025179B1/de not_active Expired
- 1980-08-27 DE DE8080105075T patent/DE3062133D1/de not_active Expired
- 1980-08-27 PT PT71743A patent/PT71743B/pt unknown
- 1980-08-27 AT AT80105075T patent/ATE2598T1/de active
- 1980-08-27 SU SU802969152A patent/SU982527A3/ru active
- 1980-09-03 JP JP12126980A patent/JPS5640692A/ja active Pending
- 1980-09-03 IL IL60956A patent/IL60956A0/xx unknown
- 1980-09-03 AU AU61984/80A patent/AU6198480A/en not_active Abandoned
- 1980-09-04 DD DD80223723A patent/DD152715A5/de unknown
- 1980-09-04 CS CS806022A patent/CS216224B2/cs unknown
- 1980-09-04 TR TR20814A patent/TR20814A/xx unknown
- 1980-09-05 BR BR8005659A patent/BR8005659A/pt unknown
- 1980-09-05 DK DK379680A patent/DK379680A/da unknown
- 1980-09-05 ZA ZA00805504A patent/ZA805504B/xx unknown
- 1980-09-05 PL PL22660180A patent/PL226601A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2936037A1 (de) | 1981-04-09 |
| AU6198480A (en) | 1981-03-12 |
| PL226601A1 (xx) | 1981-06-05 |
| TR20814A (tr) | 1982-09-15 |
| BR8005659A (pt) | 1981-03-17 |
| IL60956A0 (en) | 1980-11-30 |
| PT71743A (en) | 1980-09-01 |
| DD152715A5 (de) | 1981-12-09 |
| EP0025179A1 (de) | 1981-03-18 |
| SU982527A3 (ru) | 1982-12-15 |
| DK379680A (da) | 1981-03-07 |
| PT71743B (en) | 1981-06-15 |
| ZA805504B (en) | 1981-09-30 |
| DE3062133D1 (en) | 1983-03-31 |
| EP0025179B1 (en) | 1983-02-23 |
| ATE2598T1 (de) | 1983-03-15 |
| JPS5640692A (en) | 1981-04-16 |
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