IE43526B1 - Pyridazinyl(thiono)(thiol)phosphonic acid esters and their use as insecticides, acaricides and nematicides - Google Patents
Pyridazinyl(thiono)(thiol)phosphonic acid esters and their use as insecticides, acaricides and nematicidesInfo
- Publication number
- IE43526B1 IE43526B1 IE1855/76A IE185576A IE43526B1 IE 43526 B1 IE43526 B1 IE 43526B1 IE 1855/76 A IE1855/76 A IE 1855/76A IE 185576 A IE185576 A IE 185576A IE 43526 B1 IE43526 B1 IE 43526B1
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- carbon atoms
- formula
- alkyl
- process according
- Prior art date
Links
- 230000000895 acaricidal effect Effects 0.000 title claims abstract description 10
- 125000002098 pyridazinyl group Chemical group 0.000 title claims description 9
- 150000003008 phosphonic acid esters Chemical class 0.000 title claims description 8
- 125000003396 thiol group Chemical class [H]S* 0.000 title abstract 2
- 239000000642 acaricide Substances 0.000 title description 2
- 239000002917 insecticide Substances 0.000 title description 2
- 239000005645 nematicide Substances 0.000 title description 2
- -1 benzyloxy, benzoyloxy, phenoxy Chemical group 0.000 claims abstract description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 34
- 239000002253 acid Substances 0.000 claims abstract description 22
- 150000002148 esters Chemical class 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 150000002367 halogens Chemical class 0.000 claims abstract description 10
- 125000001424 substituent group Chemical group 0.000 claims abstract description 9
- 230000000749 insecticidal effect Effects 0.000 claims abstract description 8
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims abstract description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000005133 alkynyloxy group Chemical group 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 133
- 238000000034 method Methods 0.000 claims description 40
- 241000238631 Hexapoda Species 0.000 claims description 36
- 239000002904 solvent Substances 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 26
- 230000006378 damage Effects 0.000 claims description 18
- 241000244206 Nematoda Species 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 239000003085 diluting agent Substances 0.000 claims description 13
- 150000003573 thiols Chemical class 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 239000005864 Sulphur Substances 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001266 acyl halides Chemical class 0.000 claims description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 150000007530 organic bases Chemical group 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 150000004892 pyridazines Chemical class 0.000 claims 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims 1
- WCEGJICVJSCVFU-UHFFFAOYSA-N 2,3-dihydro-1h-pyridazin-6-one Chemical class O=C1NNCC=C1 WCEGJICVJSCVFU-UHFFFAOYSA-N 0.000 claims 1
- 230000001069 nematicidal effect Effects 0.000 abstract description 7
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical class C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 abstract description 4
- 230000000855 fungicidal effect Effects 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 37
- 239000002689 soil Substances 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000003995 emulsifying agent Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
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- 229920000151 polyglycol Polymers 0.000 description 8
- 239000010695 polyglycol Substances 0.000 description 8
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- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000047 product Substances 0.000 description 6
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- 241000500437 Plutella xylostella Species 0.000 description 5
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- 238000011156 evaluation Methods 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- VHVUTJZQFZBIRR-UHFFFAOYSA-N 1h-pyridazin-4-one Chemical class OC1=CC=NN=C1 VHVUTJZQFZBIRR-UHFFFAOYSA-N 0.000 description 4
- 241000256118 Aedes aegypti Species 0.000 description 4
- 241001124076 Aphididae Species 0.000 description 4
- DSJHVCGUBJCHTF-UHFFFAOYSA-N CCC.CC(C)P(O)(O)=O Chemical compound CCC.CC(C)P(O)(O)=O DSJHVCGUBJCHTF-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
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- 231100000053 low toxicity Toxicity 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/14—Oxygen atoms
- C07D237/16—Two oxygen atoms
-
- 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
- A01N57/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon 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)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752537353 DE2537353A1 (de) | 1975-08-21 | 1975-08-21 | Pyridazinyl(thiono)(thiol)-phosphonsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide, akarizide und nematizide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE43526L IE43526L (en) | 1977-02-21 |
| IE43526B1 true IE43526B1 (en) | 1981-03-25 |
Family
ID=5954557
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1855/76A IE43526B1 (en) | 1975-08-21 | 1976-08-20 | Pyridazinyl(thiono)(thiol)phosphonic acid esters and their use as insecticides, acaricides and nematicides |
Country Status (29)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61189287A (ja) * | 1985-02-15 | 1986-08-22 | Takeda Chem Ind Ltd | 有機リン酸エステル誘導体，その製造法および用途 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2049813A1 (de) * | 1970-10-10 | 1972-04-13 | Farbenfabriken Bayer Ag, 5090 Lever Kusen | Pyndazinothionophosphor(phosphon) säureester, Verfahren zu ihrer Herstel lung sowie ihre Verwendung als Insek tizide und Akanzide |
| DE2359661A1 (de) * | 1973-11-30 | 1975-06-05 | Bayer Ag | Pyridazin-(thiono)-thiolphosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
-
1975
- 1975-08-21 DE DE19752537353 patent/DE2537353A1/de active Pending
-
1976
- 1976-07-26 RO RO7687107A patent/RO70091A/ro unknown
- 1976-08-11 US US05/713,741 patent/US4140768A/en not_active Expired - Lifetime
- 1976-08-16 BG BG7634004A patent/BG26655A3/xx unknown
- 1976-08-17 PT PT65492A patent/PT65492B/pt unknown
- 1976-08-18 BR BR7605395A patent/BR7605395A/pt unknown
- 1976-08-18 EG EG509/76A patent/EG12403A/xx active
- 1976-08-18 DD DD194376A patent/DD127334A5/xx unknown
- 1976-08-18 NL NL7609177A patent/NL7609177A/xx not_active Application Discontinuation
- 1976-08-18 IL IL50295A patent/IL50295A0/xx unknown
- 1976-08-19 SE SE7609230A patent/SE7609230L/xx unknown
- 1976-08-19 CS CS765402A patent/CS189024B2/cs unknown
- 1976-08-19 GB GB34610/76A patent/GB1525358A/en not_active Expired
- 1976-08-19 AU AU16973/76A patent/AU1697376A/en not_active Expired
- 1976-08-19 JP JP51098259A patent/JPS5225784A/ja active Pending
- 1976-08-19 TR TR19270A patent/TR19270A/xx unknown
- 1976-08-19 SU SU762387320A patent/SU612608A3/ru active
- 1976-08-19 LU LU75625A patent/LU75625A1/xx unknown
- 1976-08-20 ES ES450850A patent/ES450850A1/es not_active Expired
- 1976-08-20 AR AR264401A patent/AR217061A1/es active
- 1976-08-20 CA CA259,589A patent/CA1080230A/en not_active Expired
- 1976-08-20 PL PL1976200477A patent/PL100332B1/pl unknown
- 1976-08-20 AT AT619676A patent/AT347180B/de active
- 1976-08-20 IE IE1855/76A patent/IE43526B1/en unknown
- 1976-08-20 ZA ZA765005A patent/ZA765005B/xx unknown
- 1976-08-20 PL PL1976200476A patent/PL100308B1/pl unknown
- 1976-08-20 FR FR7625278A patent/FR2321503A1/fr active Granted
- 1976-08-20 PL PL1976191921A patent/PL98412B1/pl unknown
- 1976-08-20 GR GR51518A patent/GR60831B/el unknown
- 1976-08-20 DK DK377076A patent/DK377076A/da unknown
- 1976-08-20 PL PL1976200478A patent/PL100333B1/pl unknown
- 1976-08-20 BE BE169964A patent/BE845383A/xx unknown
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