CH643223A5 - Dieteri idrochinonici aventi attivita ormonica giovanile e acaricida. - Google Patents
Dieteri idrochinonici aventi attivita ormonica giovanile e acaricida. Download PDFInfo
- Publication number
- CH643223A5 CH643223A5 CH579879A CH579879A CH643223A5 CH 643223 A5 CH643223 A5 CH 643223A5 CH 579879 A CH579879 A CH 579879A CH 579879 A CH579879 A CH 579879A CH 643223 A5 CH643223 A5 CH 643223A5
- Authority
- CH
- Switzerland
- Prior art keywords
- hydroquinone
- benzene
- halogen
- general formula
- compound according
- Prior art date
Links
- 230000000694 effects Effects 0.000 title description 8
- 230000000895 acaricidal effect Effects 0.000 title description 6
- 239000000642 acaricide Substances 0.000 title description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- -1 5-chloro-4-pentynyloxy Chemical group 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- 235000013601 eggs Nutrition 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 241000238631 Hexapoda Species 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 238000006704 dehydrohalogenation reaction Methods 0.000 claims description 4
- 159000000011 group IA salts Chemical class 0.000 claims description 4
- 206010061217 Infestation Diseases 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 241000607479 Yersinia pestis Species 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 3
- 235000013305 food Nutrition 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000006266 etherification reaction Methods 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 229940076134 benzene Drugs 0.000 claims 5
- NJRVQXAOVMPYSD-UHFFFAOYSA-N 1,4-bis(5,5-dichloropent-4-enoxy)benzene Chemical group ClC(Cl)=CCCCOC1=CC=C(OCCCC=C(Cl)Cl)C=C1 NJRVQXAOVMPYSD-UHFFFAOYSA-N 0.000 claims 1
- YYRGGOGFJVSOSJ-UHFFFAOYSA-N 1,4-bis(5,5-difluoropent-4-enoxy)benzene Chemical group FC(=CCCCOC1=CC=C(C=C1)OCCCC=C(F)F)F YYRGGOGFJVSOSJ-UHFFFAOYSA-N 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- FPJIQKMLLKDNHK-UHFFFAOYSA-N [O].OC1=CC=C(O)C=C1 Chemical group [O].OC1=CC=C(O)C=C1 FPJIQKMLLKDNHK-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000000460 chlorine Substances 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 241000254109 Tenebrio molitor Species 0.000 description 7
- 230000003054 hormonal effect Effects 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 241000256111 Aedes <genus> Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 230000000366 juvenile effect Effects 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 241001454293 Tetranychus urticae Species 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229930014550 juvenile hormone Natural products 0.000 description 3
- 239000002949 juvenile hormone Substances 0.000 description 3
- 150000003633 juvenile hormone derivatives Chemical class 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 150000003505 terpenes Chemical class 0.000 description 3
- IQJCJNWUQCTSBB-UHFFFAOYSA-N 1,4-bis(5-chloropent-4-ynoxy)benzene Chemical compound ClC#CCCCOC1=CC=C(OCCCC#CCl)C=C1 IQJCJNWUQCTSBB-UHFFFAOYSA-N 0.000 description 2
- ZSBDGXGICLIJGD-UHFFFAOYSA-N 4-phenoxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-UHFFFAOYSA-N 0.000 description 2
- 241000256118 Aedes aegypti Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 241001454294 Tetranychus Species 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- VZEWJVRACUZHQR-UHFFFAOYSA-N 1,1,1,5-tetrachloropentane Chemical compound ClCCCCC(Cl)(Cl)Cl VZEWJVRACUZHQR-UHFFFAOYSA-N 0.000 description 1
- WIBRQEFYLKNRTM-UHFFFAOYSA-N 1,1,5-trichloropent-1-ene Chemical compound ClCCCC=C(Cl)Cl WIBRQEFYLKNRTM-UHFFFAOYSA-N 0.000 description 1
- DMHZDOTYAVHSEH-UHFFFAOYSA-N 1-(chloromethyl)-4-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1 DMHZDOTYAVHSEH-UHFFFAOYSA-N 0.000 description 1
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
- UGBCWXMJTSSSNL-UHFFFAOYSA-N 4-(5,5-dichloropent-4-enoxy)phenol Chemical compound OC1=CC=C(OCCCC=C(Cl)Cl)C=C1 UGBCWXMJTSSSNL-UHFFFAOYSA-N 0.000 description 1
- 241001127120 Dysdercus fasciatus Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- 241000382353 Pupa Species 0.000 description 1
- 241000254112 Tribolium confusum Species 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000000843 powder Substances 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
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/16—Oxygen or sulfur directly attached to an aromatic ring system with two or more oxygen or sulfur atoms directly attached to the same aromatic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT24794/78A IT1096582B (it) | 1978-06-21 | 1978-06-21 | Dieteri idrochinonici aventi attivita' ormonica giovanile e acaricida |
IT2073479A IT1166673B (it) | 1979-03-05 | 1979-03-05 | Dieteri fenil-idrochinonici aventi attivita' ormonica giovanile e acaricida |
Publications (1)
Publication Number | Publication Date |
---|---|
CH643223A5 true CH643223A5 (it) | 1984-05-30 |
Family
ID=26327638
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH579879A CH643223A5 (it) | 1978-06-21 | 1979-06-20 | Dieteri idrochinonici aventi attivita ormonica giovanile e acaricida. |
Country Status (5)
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2023591B (en) * | 1978-06-21 | 1982-10-06 | Montedison Spa | Hydroquinone diethers having a juvenile hormonic and acaricide activity |
IT1218326B (it) * | 1982-07-23 | 1990-04-12 | Montedison Spa | 1-fenossi (feniltio)-4-arilalchinil ossi-benzene derivati ad azione ormonica giovanile ed acaricida |
JPH0749379B2 (ja) * | 1985-12-27 | 1995-05-31 | 住友化学工業株式会社 | 置換ベンゼン誘導体およびそれを有効成分とする農園芸用殺菌剤 |
US5155196A (en) * | 1987-06-01 | 1992-10-13 | The Dow Chemical Company | Polymer resulting from the cure of a preformed chromene-containing mixture |
JPH01503541A (ja) * | 1987-06-01 | 1989-11-30 | ザ ダウ ケミカル カンパニー | ヒドロキシ芳香族化合物のプロパルギルエーテルの製造方法 |
MX9306614A (es) * | 1992-10-23 | 1994-04-29 | Dennis Mark Henderson | Composicion de metodos para la formacion de un insecticida. |
US5939061A (en) * | 1994-12-07 | 1999-08-17 | The United States Of America, As Represented By The Secretary Of Agriculture | Ant bait attractive to multiple species of ants |
US7037494B2 (en) | 1997-10-14 | 2006-05-02 | The Board Of Regents Of The University Of Texas System | Formulations and methods for insect control |
BR0308619B1 (pt) * | 2002-03-22 | 2012-10-02 | recipiente de isca hermeticamente vedado e método para reduzir ou eliminar uma população de cupins. | |
US7293618B2 (en) * | 2004-03-12 | 2007-11-13 | National-Oilwell, L.P. | Power slip for drillpipe |
US8084052B1 (en) | 2008-02-26 | 2011-12-27 | Mason James W | Chemical composition for controlling insects |
CN103190203A (zh) | 2010-12-28 | 2013-07-03 | 株式会社小金井 | 离子发生装置 |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3322813A (en) * | 1962-06-30 | 1967-05-30 | Meiji Seika Kaisha | Halopropargyl aryl ether compounds |
US3379755A (en) * | 1964-06-04 | 1968-04-23 | Merck & Co Inc | Preparation of (4-alkanoylphenoxy) acetic acids by oxidation |
US3816541A (en) * | 1970-11-16 | 1974-06-11 | Stauffer Chemical Co | Aryl acetylene ethers |
BE794894A (fr) * | 1972-02-04 | 1973-08-02 | Ciba Geigy | Ethers aryliques et produits pesticides |
US4141921A (en) * | 1972-02-09 | 1979-02-27 | Ciba-Geigy Corporation | Phenoxyphenyl- and phenoxybenzyl-alkynyl ethers |
CH568715A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-03-16 | 1975-11-14 | Ciba Geigy Ag | |
US4061683A (en) * | 1973-01-31 | 1977-12-06 | Ciba-Geigy Corporation | Diphenyl ether derivatives |
US4153731A (en) * | 1973-04-18 | 1979-05-08 | Ciba-Geigy Corporation | Phenoxy (benzyloxy/benzylthio) benzene derivatives |
DE2528314A1 (de) * | 1974-06-28 | 1976-01-15 | Ciba Geigy Ag | Phenylalkinylaether-derivate |
IT1059127B (it) * | 1976-04-15 | 1982-05-31 | Montedison Spa | Eteri e tioeteri benzilici o feni lici a catena alifatica lineare con terminale alogenato ad attivi ta ormonica giovanile e acaric/da |
IT1096582B (it) * | 1978-06-21 | 1985-08-26 | Montedison Spa | Dieteri idrochinonici aventi attivita' ormonica giovanile e acaricida |
GB2023591B (en) * | 1978-06-21 | 1982-10-06 | Montedison Spa | Hydroquinone diethers having a juvenile hormonic and acaricide activity |
-
1979
- 1979-06-20 GB GB7921469A patent/GB2023591B/en not_active Expired
- 1979-06-20 CH CH579879A patent/CH643223A5/it not_active IP Right Cessation
- 1979-06-21 DE DE19792925113 patent/DE2925113A1/de active Granted
-
1980
- 1980-10-20 US US06/198,488 patent/US4356329A/en not_active Expired - Lifetime
- 1980-10-20 US US06/198,489 patent/US4334104A/en not_active Expired - Lifetime
-
1982
- 1982-04-05 FR FR828205863A patent/FR2522650B1/fr not_active Expired
- 1982-05-17 US US06/379,177 patent/US4460606A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
US4460606A (en) | 1984-07-17 |
GB2023591A (en) | 1980-01-03 |
FR2522650A1 (fr) | 1983-09-09 |
DE2925113A1 (de) | 1980-01-10 |
DE2925113C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-08-24 |
US4356329A (en) | 1982-10-26 |
US4334104A (en) | 1982-06-08 |
FR2522650B1 (fr) | 1985-07-26 |
GB2023591B (en) | 1982-10-06 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PL | Patent ceased |