CA1151064A - Oxadiazoles substitues et leur utilisation pour l'extermination des iules, puces de terre et vers - Google Patents
Oxadiazoles substitues et leur utilisation pour l'extermination des iules, puces de terre et versInfo
- Publication number
- CA1151064A CA1151064A CA000374489A CA374489A CA1151064A CA 1151064 A CA1151064 A CA 1151064A CA 000374489 A CA000374489 A CA 000374489A CA 374489 A CA374489 A CA 374489A CA 1151064 A CA1151064 A CA 1151064A
- Authority
- CA
- Canada
- Prior art keywords
- insecticides
- sulfur
- compound
- wire
- grub
- 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.)
- Expired
Links
- 241001136249 Agriotes lineatus Species 0.000 title claims abstract description 15
- 239000002917 insecticide Substances 0.000 title abstract description 11
- 241000738498 Epitrix pubescens Species 0.000 title abstract description 7
- 150000004866 oxadiazoles Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 239000002689 soil Substances 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 17
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- 239000011593 sulfur Substances 0.000 claims abstract description 14
- 239000001301 oxygen Substances 0.000 claims abstract description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 11
- 241000902876 Alticini Species 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- FRYPWUYDPUBMRU-UHFFFAOYSA-N 2-[(4-chlorophenoxy)methyl]-5-(2,4-dichloro-5-fluorophenyl)-1,3,4-oxadiazole Chemical class C1=C(Cl)C(F)=CC(C=2OC(COC=3C=CC(Cl)=CC=3)=NN=2)=C1Cl FRYPWUYDPUBMRU-UHFFFAOYSA-N 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 230000000749 insecticidal effect Effects 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 241000238631 Hexapoda Species 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 241000500845 Costelytra zealandica Species 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 241000254173 Coleoptera Species 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 241000238876 Acari Species 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241001427543 Elateridae Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 241001124076 Aphididae Species 0.000 description 2
- 241001124134 Chrysomelidae Species 0.000 description 2
- 241000683561 Conoderus Species 0.000 description 2
- 241000256113 Culicidae Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 244000017020 Ipomoea batatas Species 0.000 description 2
- 235000002678 Ipomoea batatas Nutrition 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 241001608567 Phaedon cochleariae Species 0.000 description 2
- 241000254062 Scarabaeidae Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 241001611608 Systena Species 0.000 description 2
- ZWIFYHVITGYSLO-UHFFFAOYSA-N diethoxy-[(3-methyl-1,2,4-oxadiazol-5-yl)methylsulfanyl]-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(=S)(OCC)SCC1=NC(C)=NO1 ZWIFYHVITGYSLO-UHFFFAOYSA-N 0.000 description 2
- 235000021186 dishes Nutrition 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 2
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N gamma-hexachlorocyclohexane Natural products ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 2
- JLYXXMFPNIAWKQ-GNIYUCBRSA-N gamma-hexachlorocyclohexane Chemical compound Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl JLYXXMFPNIAWKQ-GNIYUCBRSA-N 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000003359 percent control normalization Methods 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- FRUIHNKZQIULDG-UHFFFAOYSA-N 2-[5-(chloromethyl)-3-methyl-2h-1,2,4-oxadiazol-3-yl]-n'-hydroxyethanimidamide Chemical compound ON=C(N)CC1(C)NOC(CCl)=N1 FRUIHNKZQIULDG-UHFFFAOYSA-N 0.000 description 1
- SOAUOABDYBGOQY-UHFFFAOYSA-N 5-chloro-2,3-dimethyl-3h-1,2,4-oxadiazole Chemical compound CC1N=C(Cl)ON1C SOAUOABDYBGOQY-UHFFFAOYSA-N 0.000 description 1
- 241001136265 Agriotes Species 0.000 description 1
- 241000169953 Blapstinus Species 0.000 description 1
- QCHVEUFFZBSFKR-UHFFFAOYSA-N C(C)#N.C(C)(N)=NO Chemical compound C(C)#N.C(C)(N)=NO QCHVEUFFZBSFKR-UHFFFAOYSA-N 0.000 description 1
- JMVSBZNQHOZUBB-UHFFFAOYSA-N CC1=NOC(=N1)CCl.CC1=NOC(=N1)CSP(=S)(OCC)OCC Chemical compound CC1=NOC(=N1)CCl.CC1=NOC(=N1)CSP(=S)(OCC)OCC JMVSBZNQHOZUBB-UHFFFAOYSA-N 0.000 description 1
- 239000005745 Captan Substances 0.000 description 1
- 241000902406 Chaetocnema Species 0.000 description 1
- 241000500864 Costelytra Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000242268 Ctenicera Species 0.000 description 1
- 241000721035 Diaprepes Species 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 241001105160 Eleodes Species 0.000 description 1
- 241000551596 Eleodes hispilabris Species 0.000 description 1
- 241000510032 Ellipsaria lineolata Species 0.000 description 1
- 241000303278 Epitrix Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241001227244 Heteronychus Species 0.000 description 1
- 241001260426 Horistonotus Species 0.000 description 1
- 241000683448 Limonius Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 241000077345 Mycetophylax auritus Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000488583 Panonychus ulmi Species 0.000 description 1
- 241001325166 Phacelia congesta Species 0.000 description 1
- 241001640279 Phyllophaga Species 0.000 description 1
- 241000255969 Pieris brassicae Species 0.000 description 1
- 241000500437 Plutella xylostella Species 0.000 description 1
- 241000254103 Popillia Species 0.000 description 1
- 235000005805 Prunus cerasus Nutrition 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- 241000344246 Tetranychus cinnabarinus Species 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- HFRHTRKMBOQLLL-UHFFFAOYSA-N azane;diethoxy-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound [NH4+].CCOP([S-])(=S)OCC HFRHTRKMBOQLLL-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229940117949 captan Drugs 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- NZRHZQGDTLNQFM-UHFFFAOYSA-N diethoxy-[(3-methyl-1,2-oxazol-5-yl)methylsulfanyl]-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(=S)(OCC)SCC1=CC(C)=NO1 NZRHZQGDTLNQFM-UHFFFAOYSA-N 0.000 description 1
- IFNMAVHRIJFMJW-UHFFFAOYSA-N diethoxy-[(5-methyl-1,2,4-oxadiazol-3-yl)methylsulfanyl]-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(=S)(OCC)SCC1=NOC(C)=N1 IFNMAVHRIJFMJW-UHFFFAOYSA-N 0.000 description 1
- -1 e.g. Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229960002809 lindane Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AEXITZJSLGALNH-UHFFFAOYSA-N n'-hydroxyethanimidamide Chemical compound CC(N)=NO AEXITZJSLGALNH-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
- C07F9/653—Five-membered rings
- C07F9/65306—Five-membered rings containing two nitrogen atoms
- C07F9/65318—Five-membered rings containing two nitrogen atoms having the two nitrogen atoms in positions 1 and 3
-
- 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
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US143,566 | 1980-04-25 | ||
| US06/143,567 US4308261A (en) | 1980-04-25 | 1980-04-25 | Substituted oxadiazoles and their use as wire worm and flea beetle insecticides |
| US06/143,566 US4308260A (en) | 1980-04-25 | 1980-04-25 | Substituted oxadiazoles and their use as grub insecticides |
| US143,567 | 1980-04-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1151064A true CA1151064A (fr) | 1983-08-02 |
Family
ID=26841167
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000374489A Expired CA1151064A (fr) | 1980-04-25 | 1981-04-02 | Oxadiazoles substitues et leur utilisation pour l'extermination des iules, puces de terre et vers |
Country Status (5)
| Country | Link |
|---|---|
| AU (1) | AU6952881A (fr) |
| CA (1) | CA1151064A (fr) |
| DE (1) | DE3116449A1 (fr) |
| FR (1) | FR2481070A1 (fr) |
| GB (1) | GB2074450B (fr) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1451294A (fr) * | 1965-05-18 | 1966-01-07 | Rhone Poulenc Sa | Nouveaux esters phosphoriques, leur préparation et leur emploi |
| US4237121A (en) * | 1979-06-14 | 1980-12-02 | Chevron Research Company | Substituted oxadiazoles and their use as corn root worm insecticides |
-
1981
- 1981-04-02 CA CA000374489A patent/CA1151064A/fr not_active Expired
- 1981-04-14 GB GB8111820A patent/GB2074450B/en not_active Expired
- 1981-04-14 AU AU69528/81A patent/AU6952881A/en not_active Abandoned
- 1981-04-23 FR FR8108100A patent/FR2481070A1/fr active Pending
- 1981-04-24 DE DE19813116449 patent/DE3116449A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| FR2481070A1 (fr) | 1981-10-30 |
| GB2074450B (en) | 1983-04-07 |
| AU6952881A (en) | 1981-10-29 |
| GB2074450A (en) | 1981-11-04 |
| DE3116449A1 (de) | 1982-01-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |