CA1082205A - Miticidal and aphicidal 2-higher alkyl-3-hydroxy-1,4- naphthaquinone carboxylic acid esters - Google Patents
Miticidal and aphicidal 2-higher alkyl-3-hydroxy-1,4- naphthaquinone carboxylic acid estersInfo
- Publication number
- CA1082205A CA1082205A CA261,032A CA261032A CA1082205A CA 1082205 A CA1082205 A CA 1082205A CA 261032 A CA261032 A CA 261032A CA 1082205 A CA1082205 A CA 1082205A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- carbon atoms
- alkyl
- mites
- plant
- 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
- 230000003129 miticidal effect Effects 0.000 title abstract description 9
- 230000002824 aphicidal effect Effects 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 62
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 32
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims abstract description 23
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 16
- 239000000460 chlorine Chemical group 0.000 claims abstract description 9
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000011737 fluorine Chemical group 0.000 claims abstract description 6
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 3
- 241000238876 Acari Species 0.000 claims description 22
- 241001124076 Aphididae Species 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- STUSTWKEFDQFFZ-UHFFFAOYSA-N Chlordimeform Chemical compound CN(C)C=NC1=CC=C(Cl)C=C1C STUSTWKEFDQFFZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 claims description 3
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 claims description 2
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 claims description 2
- ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
- 241000607479 Yersinia pestis Species 0.000 abstract description 5
- 241001465754 Metazoa Species 0.000 abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 150000002500 ions Chemical class 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- 239000002253 acid Substances 0.000 description 6
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- -1 3-propio Chemical class 0.000 description 4
- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000207199 Citrus Species 0.000 description 3
- 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 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229930192627 Naphthoquinone Natural products 0.000 description 3
- 239000000642 acaricide Substances 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 235000020971 citrus fruits Nutrition 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000002791 naphthoquinones Chemical class 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 241000894007 species Species 0.000 description 3
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 2
- 229910000497 Amalgam Inorganic materials 0.000 description 2
- 244000144730 Amygdalus persica Species 0.000 description 2
- 241000398201 Bryobia praetiosa Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 241000488583 Panonychus ulmi Species 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000006040 Prunus persica var persica Nutrition 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 240000001987 Pyrus communis Species 0.000 description 2
- 241000344246 Tetranychus cinnabarinus Species 0.000 description 2
- 241000488530 Tetranychus pacificus Species 0.000 description 2
- 241000916142 Tetranychus turkestani Species 0.000 description 2
- 241001454293 Tetranychus urticae Species 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
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- 239000003480 eluent Substances 0.000 description 2
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- 231100000518 lethal Toxicity 0.000 description 2
- 230000001665 lethal effect Effects 0.000 description 2
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 2
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- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- GHPYJLCQYMAXGG-WCCKRBBISA-N (2R)-2-amino-3-(2-boronoethylsulfanyl)propanoic acid hydrochloride Chemical compound Cl.N[C@@H](CSCCB(O)O)C(O)=O GHPYJLCQYMAXGG-WCCKRBBISA-N 0.000 description 1
- 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
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 description 1
- DRTQHJPVMGBUCF-UCVXFZOQSA-N 1-[(2s,3s,4s,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O[C@H]1[C@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UCVXFZOQSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- LSKONYYRONEBKA-UHFFFAOYSA-N 2-Dodecanone Natural products CCCCCCCCCCC(C)=O LSKONYYRONEBKA-UHFFFAOYSA-N 0.000 description 1
- ACDHBFFJCFHSMB-UHFFFAOYSA-N 3-dodecyl-4-hydroxynaphthalene-1,2-dione Chemical compound C1=CC=C2C(=O)C(=O)C(CCCCCCCCCCCC)=C(O)C2=C1 ACDHBFFJCFHSMB-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
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- 101100451306 Caenorhabditis elegans hnd-1 gene Proteins 0.000 description 1
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- 239000005746 Carboxin Substances 0.000 description 1
- 101000654316 Centruroides limpidus Beta-toxin Cll2 Proteins 0.000 description 1
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- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
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- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
- C07C46/06—Preparation of quinones by oxidation giving rise to quinoid structures of at least one hydroxy group on a six-membered aromatic ring
- C07C46/08—Preparation of quinones by oxidation giving rise to quinoid structures of at least one hydroxy group on a six-membered aromatic ring with molecular oxygen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
- C07C37/002—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain by transformation of a functional group, e.g. oxo, carboxyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
- C07C46/04—Preparation of quinones by oxidation giving rise to quinoid structures of unsubstituted ring carbon atoms in six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
- C07C46/06—Preparation of quinones by oxidation giving rise to quinoid structures of at least one hydroxy group on a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/02—Preparation of esters of carbonic or haloformic acids from phosgene or haloformates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US613,553 | 1975-09-15 | ||
| US05/613,553 US4055661A (en) | 1974-12-11 | 1975-09-15 | Miticidal and aphicidal method utilizing 2-higher alkyl-3-hydroxy-1,4-naphthoquinone carboxylic acid esters |
| US05/671,044 US4070481A (en) | 1975-09-15 | 1976-03-29 | Substituted 2-higher alkyl-3-hydroxy-1,4-naphthoquinone carboxylic acid esters and their use as miticides |
| US05/681,594 US4082848A (en) | 1975-09-15 | 1976-04-29 | 2-higher alkyl-3-hydroxy-1,4-naphthoquinone carboxylic acid esters |
| US681,594 | 1976-04-29 | ||
| US671,044 | 1991-03-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1082205A true CA1082205A (en) | 1980-07-22 |
Family
ID=27417111
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA261,032A Expired CA1082205A (en) | 1975-09-15 | 1976-09-13 | Miticidal and aphicidal 2-higher alkyl-3-hydroxy-1,4- naphthaquinone carboxylic acid esters |
Country Status (15)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9155302B2 (en) | 2005-04-28 | 2015-10-13 | Bayer Intellectual Property Gmbh | Active substance combinations |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL56013A (en) * | 1977-11-22 | 1983-06-15 | Wellcome Found | 2-cycloalkyl-3-hydroxy-1,4-naphthoquinone derivatives,their preparation and therapeutic compositions containing them |
| GB8310140D0 (en) | 1983-04-14 | 1983-05-18 | Wellcome Found | Antiprotozoal agents |
| US5053432A (en) * | 1983-04-14 | 1991-10-01 | Burroughs Wellcome Co. | Naphthoquinone derivatives |
| US4980489A (en) * | 1988-02-23 | 1990-12-25 | Kawasaki Kasei Chemicals Ltd. | 2-(1-alkylaminoalkyl)-3-hydroxy-1,4-naphthoquinone |
| JPH01233201A (ja) * | 1988-03-15 | 1989-09-19 | Aguro Kanesho Kk | ２−（アセチルオキシ）−３−ドデシル−１，４−ナフタレンジオンの殺ダニ活性を増強させる方法 |
| WO1996021354A1 (en) * | 1995-01-10 | 1996-07-18 | British Technology Group Limited | Pesticidal compounds |
| RU2180330C2 (ru) * | 1995-01-10 | 2002-03-10 | Бритиш текнолоджи груп лимитед | 1,2,3,4-замещенные нафталиновые соединения, способ их получения, способ борьбы с вредителями, пестицидная композиция |
| KR19980701323A (ko) * | 1995-01-10 | 1998-05-15 | 말콤 카터 | 해충구제용 화합물(pesticidal compounds) |
| DE10319590A1 (de) | 2003-05-02 | 2004-11-18 | Bayer Cropscience Ag | Wirkstoffkombinationen mit nematiziden und insektiziden Eigenschaften basierend auf Trifluorbutenyl-Verbindungen |
| DE10319591A1 (de) | 2003-05-02 | 2004-11-18 | Bayer Cropscience Ag | Wirkstoffkombinationen mit nematiziden, insektiziden und fungiziden Eigenschaften basierend auf Trifluorbutenyl-Verbindungen |
| DE10330723A1 (de) | 2003-07-08 | 2005-02-03 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| DE10330724A1 (de) | 2003-07-08 | 2005-01-27 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| DE10353281A1 (de) | 2003-11-14 | 2005-06-16 | Bayer Cropscience Ag | Wirkstoffkombination mit insektiziden und akariziden Eigenschaften |
| DE102004021564A1 (de) | 2003-11-14 | 2005-07-07 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden Eigenschaften |
| WO2005053406A1 (de) | 2003-12-04 | 2005-06-16 | Bayer Cropscience Aktiengesellschaft | Wirkstoffkombinationen mit insektiziden eigenschaften |
| DE10356550A1 (de) | 2003-12-04 | 2005-07-07 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden Eigenschaften |
| US8821898B2 (en) | 2003-12-04 | 2014-09-02 | Bayer Cropscience Ag | Active compound combinations having insecticidal and acaricidal properties |
| DE102004001271A1 (de) | 2004-01-08 | 2005-08-04 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden Eigenschaften |
| JP2006076990A (ja) | 2004-03-12 | 2006-03-23 | Bayer Cropscience Ag | 殺虫性ベンゼンジカルボキサミド類 |
| GB0704652D0 (en) * | 2007-03-09 | 2007-04-18 | Syngenta Participations Ag | Novel herbicides |
| DE102007045922A1 (de) | 2007-09-26 | 2009-04-02 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| US8404260B2 (en) | 2008-04-02 | 2013-03-26 | Bayer Cropscience Lp | Synergistic pesticide compositions |
| EP2127522A1 (de) | 2008-05-29 | 2009-12-02 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| EP2382865A1 (de) | 2010-04-28 | 2011-11-02 | Bayer CropScience AG | Synergistische Wirkstoffkombinationen |
| CN102726411B (zh) * | 2011-04-12 | 2013-12-11 | 深圳诺普信农化股份有限公司 | 一种杀螨剂及其应用 |
| IL301822A (en) | 2020-09-30 | 2023-06-01 | Control Solutions Inc | Powder pest control compositions and methods of using |
| CA3210634A1 (en) | 2021-03-01 | 2022-09-09 | Ian Rodriguez | Solid particulate pest control compositions and methods |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR7502659A (pt) * | 1974-05-10 | 1976-03-16 | Du Pont | Processo e composicao para a protecao de plantas contra acaros ou afideos |
-
1976
- 1976-08-30 FI FI762480A patent/FI762480A7/fi not_active Application Discontinuation
- 1976-09-13 CA CA261,032A patent/CA1082205A/en not_active Expired
- 1976-09-13 JP JP51108922A patent/JPS5248648A/ja active Pending
- 1976-09-14 NL NL7610199A patent/NL7610199A/xx not_active Application Discontinuation
- 1976-09-14 DE DE19762641343 patent/DE2641343A1/de not_active Withdrawn
- 1976-09-14 FR FR7627561A patent/FR2323676A1/fr active Granted
- 1976-09-14 TR TR19528A patent/TR19528A/xx unknown
- 1976-09-14 DK DK413976A patent/DK413976A/da not_active Application Discontinuation
- 1976-09-14 GB GB38052/76A patent/GB1518750A/en not_active Expired
- 1976-09-14 NZ NZ182051A patent/NZ182051A/xx unknown
- 1976-09-14 EG EG558/76A patent/EG12508A/xx active
- 1976-09-15 AU AU17735/76A patent/AU1773576A/en not_active Expired - Fee Related
- 1976-09-15 NO NO763151A patent/NO146155C/no unknown
- 1976-09-15 PH PH18911A patent/PH13146A/en unknown
- 1976-09-15 CH CH1171976A patent/CH629651A5/de not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9155302B2 (en) | 2005-04-28 | 2015-10-13 | Bayer Intellectual Property Gmbh | Active substance combinations |
Also Published As
| Publication number | Publication date |
|---|---|
| NO146155C (no) | 1982-08-11 |
| NO146155B (no) | 1982-05-03 |
| DK413976A (da) | 1977-03-16 |
| AU1773576A (en) | 1978-03-23 |
| JPS5248648A (en) | 1977-04-18 |
| EG12508A (en) | 1981-12-31 |
| DE2641343A1 (de) | 1977-04-07 |
| TR19528A (tr) | 1979-07-06 |
| NO763151L (enrdf_load_stackoverflow) | 1977-03-16 |
| FI762480A7 (enrdf_load_stackoverflow) | 1977-03-16 |
| GB1518750A (en) | 1978-07-26 |
| CH629651A5 (en) | 1982-05-14 |
| NZ182051A (en) | 1978-09-25 |
| FR2323676A1 (fr) | 1977-04-08 |
| FR2323676B1 (enrdf_load_stackoverflow) | 1980-12-05 |
| NL7610199A (nl) | 1977-03-17 |
| PH13146A (en) | 1979-12-18 |
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Legal Events
| Date | Code | Title | Description |
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| MKEX | Expiry |