IL89274A - Process for preparing environmentally safe dicofol - Google Patents
Process for preparing environmentally safe dicofolInfo
- Publication number
- IL89274A IL89274A IL8927489A IL8927489A IL89274A IL 89274 A IL89274 A IL 89274A IL 8927489 A IL8927489 A IL 8927489A IL 8927489 A IL8927489 A IL 8927489A IL 89274 A IL89274 A IL 89274A
- Authority
- IL
- Israel
- Prior art keywords
- dicofol
- ddt
- technical
- ddtr
- acetic acid
- Prior art date
Links
- UOAMTSKGCBMZTC-UHFFFAOYSA-N dicofol Chemical compound C=1C=C(Cl)C=CC=1C(C(Cl)(Cl)Cl)(O)C1=CC=C(Cl)C=C1 UOAMTSKGCBMZTC-UHFFFAOYSA-N 0.000 title claims abstract description 66
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 44
- 239000000203 mixture Substances 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 26
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 125000005233 alkylalcohol group Chemical group 0.000 claims abstract description 7
- YVGGHNCTFXOJCH-UHFFFAOYSA-N DDT Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 YVGGHNCTFXOJCH-UHFFFAOYSA-N 0.000 claims description 28
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 16
- 229960000583 acetic acid Drugs 0.000 claims description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- 239000013078 crystal Substances 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 239000012362 glacial acetic acid Substances 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims 2
- 238000002156 mixing Methods 0.000 claims 2
- 239000011369 resultant mixture Substances 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 238000009472 formulation Methods 0.000 abstract description 14
- JOQCINXYMZALAZ-UHFFFAOYSA-N 1-chloro-4-[1,2,2,2-tetrachloro-1-(4-chlorophenyl)ethyl]benzene Chemical compound C1=CC(Cl)=CC=C1C(Cl)(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 JOQCINXYMZALAZ-UHFFFAOYSA-N 0.000 abstract description 7
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract 2
- 239000000243 solution Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 241000238876 Acari Species 0.000 description 7
- 238000013459 approach Methods 0.000 description 7
- 239000012535 impurity Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000004563 wettable powder Substances 0.000 description 5
- LUXSISXJGNCOKN-UHFFFAOYSA-N 2,2,2-trichloro-1-(2-chlorophenyl)-1-(4-chlorophenyl)ethanol Chemical compound C=1C=CC=C(Cl)C=1C(C(Cl)(Cl)Cl)(O)C1=CC=C(Cl)C=C1 LUXSISXJGNCOKN-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000011149 active material Substances 0.000 description 3
- 238000010960 commercial process Methods 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 229960004592 isopropanol Drugs 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- -1 alkyl phenol Chemical compound 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 229960003750 ethyl chloride Drugs 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- 235000012907 honey Nutrition 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- ZBJVLWIYKOAYQH-UHFFFAOYSA-N naphthalen-2-yl 2-hydroxybenzoate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=C(C=CC=C2)C2=C1 ZBJVLWIYKOAYQH-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- YXMYPHLWXBXNFF-UHFFFAOYSA-N (2-chlorophenyl)-(4-chlorophenyl)methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1Cl YXMYPHLWXBXNFF-UHFFFAOYSA-N 0.000 description 1
- JKTAIYGNOFSMCE-UHFFFAOYSA-N 2,3-di(nonyl)phenol Chemical compound CCCCCCCCCC1=CC=CC(O)=C1CCCCCCCCC JKTAIYGNOFSMCE-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 101001098982 Homo sapiens Propionyl-CoA carboxylase beta chain, mitochondrial Proteins 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 102100039025 Propionyl-CoA carboxylase beta chain, mitochondrial Human genes 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- QPFMBZIOSGYJDE-UHFFFAOYSA-N acetylene tetrachloride Natural products ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- NEMFQSKAPLGFIP-UHFFFAOYSA-N magnesiosodium Chemical compound [Na].[Mg] NEMFQSKAPLGFIP-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000003129 miticidal effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/78—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by condensation or crystallisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Detergent Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL8927489A IL89274A (en) | 1989-02-13 | 1989-02-13 | Process for preparing environmentally safe dicofol |
| EP90101212A EP0383054B1 (en) | 1989-02-13 | 1990-01-22 | A process for preparing environmentally safe dicofol and its formulations |
| AT90101212T ATE124384T1 (de) | 1989-02-13 | 1990-01-22 | Verfahren zur herstellung von für die umwelt unbedenklichem dicofol und dessen formulierungen. |
| ES90101212T ES2073461T3 (es) | 1989-02-13 | 1990-01-22 | Procedimiento para preparar dicofol inocuo para el medio ambiente y sus formulaciones. |
| DE69020377T DE69020377T2 (de) | 1989-02-13 | 1990-01-22 | Verfahren zur Herstellung von für die Umwelt unbedenklichem Dicofol und dessen Formulierungen. |
| IN90/CAL/90A IN170240B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-02-13 | 1990-01-30 | |
| JP2031306A JPH02240035A (ja) | 1989-02-13 | 1990-02-09 | 環境的に安全なジコホールの製造方法とその組成物 |
| BR909000709A BR9000709A (pt) | 1989-02-13 | 1990-02-13 | Processo para prepar p,p'-dicofol livre de ddtr,p,p'-dicofol,composicoes acaricidas livres de ddtr e metodo para controlar acaros |
| US07/611,396 US5118881A (en) | 1989-02-13 | 1990-11-08 | Process for preparing environmentally safe dicofol and its formulations |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL8927489A IL89274A (en) | 1989-02-13 | 1989-02-13 | Process for preparing environmentally safe dicofol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL89274A0 IL89274A0 (en) | 1989-09-10 |
| IL89274A true IL89274A (en) | 1994-04-12 |
Family
ID=11059684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL8927489A IL89274A (en) | 1989-02-13 | 1989-02-13 | Process for preparing environmentally safe dicofol |
Country Status (9)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL89274A (en) * | 1989-02-13 | 1994-04-12 | Agan Chemical Manufacturers | Process for preparing environmentally safe dicofol |
| DE69017965T2 (de) * | 1989-07-18 | 1995-11-16 | Elf Atochem S.A., Puteaux, Hauts-De-Seine | Verfahren zur Reinigung von 1,1-bis(4-chlorphenyl)-2,2,2-trichlorethanol. |
| JP2931096B2 (ja) * | 1990-06-22 | 1999-08-09 | エルフ アトケム ソシエテ アノニム | １，１―ビス（クロロフェニル）―２，２，２―トリクロロエタノールの合成方法 |
| JP5157478B2 (ja) | 2008-01-25 | 2013-03-06 | ダイキン工業株式会社 | オレフィン−アルコール共沸混合物の分離方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2812362A (en) * | 1955-10-12 | 1957-11-05 | Rohm & Haas | Preparation of bis (chlorophenyl)-trichloroethanol |
| EP0065354B1 (en) * | 1981-05-12 | 1985-07-03 | Imperial Chemical Industries Plc | Process for the preparation of 1,1-bis phenyl-2-haloalkan-1-ols |
| US4705902A (en) * | 1985-10-03 | 1987-11-10 | Rohm And Haas Company | DDTR-free 1,1-bis(chlorophenyl)-2,2,2-trichloroethanol |
| IL89274A (en) * | 1989-02-13 | 1994-04-12 | Agan Chemical Manufacturers | Process for preparing environmentally safe dicofol |
-
1989
- 1989-02-13 IL IL8927489A patent/IL89274A/en not_active IP Right Cessation
-
1990
- 1990-01-22 EP EP90101212A patent/EP0383054B1/en not_active Expired - Lifetime
- 1990-01-22 DE DE69020377T patent/DE69020377T2/de not_active Expired - Fee Related
- 1990-01-22 ES ES90101212T patent/ES2073461T3/es not_active Expired - Lifetime
- 1990-01-22 AT AT90101212T patent/ATE124384T1/de not_active IP Right Cessation
- 1990-01-30 IN IN90/CAL/90A patent/IN170240B/en unknown
- 1990-02-09 JP JP2031306A patent/JPH02240035A/ja active Pending
- 1990-02-13 BR BR909000709A patent/BR9000709A/pt not_active IP Right Cessation
- 1990-11-08 US US07/611,396 patent/US5118881A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES2073461T3 (es) | 1995-08-16 |
| IN170240B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-02-29 |
| BR9000709A (pt) | 1991-01-22 |
| DE69020377D1 (de) | 1995-08-03 |
| IL89274A0 (en) | 1989-09-10 |
| EP0383054A3 (en) | 1992-01-29 |
| US5118881A (en) | 1992-06-02 |
| JPH02240035A (ja) | 1990-09-25 |
| EP0383054A2 (en) | 1990-08-22 |
| ATE124384T1 (de) | 1995-07-15 |
| EP0383054B1 (en) | 1995-06-28 |
| DE69020377T2 (de) | 1995-12-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FR2494688A1 (fr) | Nouvelles 2-(1-(oxyamino)-alkylidene)-cyclohexane-1,3-diones substituees et compositions herbicides les contenant | |
| IL89274A (en) | Process for preparing environmentally safe dicofol | |
| EP0011091A1 (de) | Verfahren zur Herstellung von Alkyl- bzw. Arylthiomethyl-phenolen | |
| US4141921A (en) | Phenoxyphenyl- and phenoxybenzyl-alkynyl ethers | |
| BE882335A (fr) | Isomere geometrique de 1-triazolyl-styrenes substitues en poisition 1, leur preparation et leur utilisation comme fongicides, herbicides et/ou regulateurs de la croissance des plantes | |
| HU195635B (en) | Process for preparing 5-/2,5-dimethyl-phenoxy/-2,2-dimethyl-pentane acid | |
| US2759972A (en) | 2-amino and acylamino-1-(hydrocarbylsulphonylphenyl)-1, 3-propanediols | |
| US2861915A (en) | Dinitrophenyl 4-pentenoates | |
| US2823224A (en) | Haloaryloxyalkyl esters of alpha, alpha-dichlorobutyric acid | |
| US4992471A (en) | Molluscicides | |
| IL41437A (en) | Phenyl and benzyl alkynyl ethers their production and pest-population control compositions containing them | |
| US3862327A (en) | Substituted phenylethyl sulfites useful for controlling mites | |
| US2862022A (en) | Dinitroalkylphenyl methacrylates | |
| US3775458A (en) | Substituted phenylethyl sulfites | |
| JPH07196411A (ja) | 菌・カビ類の防除法 | |
| FR2560007A1 (fr) | Compositions fongicides comprenant des derives de phenoxy benzaldehyde | |
| US3388167A (en) | Beta-bromo-ethyl aryl thio-ethers | |
| FR2543142A1 (fr) | Ester de l'hydroxyde de tricyclohexyletain acaricide | |
| EP0101570B1 (en) | Method for the resolution of racemic 2-cp-difluoromethoxy phenyl)-3-methylbutyric acid | |
| BE826376A (fr) | Dinitroanilines | |
| US3251875A (en) | N-nitroso derivatives | |
| US2464176A (en) | N-aralkyl-alkylamine salts of chlorophenols | |
| US3142556A (en) | Controlling vegetation with pyrrolidinylcarboxylates | |
| BE852417Q (fr) | Application de composes cycliques a la lutte contre des depredateurs | |
| US3402209A (en) | Insecticidal tertiary alcohols |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RH | Patent void |