IL33455A - 2,4-dinitro-6-alkylphenyl-ethers and acaricidal preparations containing them - Google Patents
2,4-dinitro-6-alkylphenyl-ethers and acaricidal preparations containing themInfo
- Publication number
- IL33455A IL33455A IL33455A IL3345569A IL33455A IL 33455 A IL33455 A IL 33455A IL 33455 A IL33455 A IL 33455A IL 3345569 A IL3345569 A IL 3345569A IL 33455 A IL33455 A IL 33455A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- compound
- residue
- butyl
- hydrogen atom
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 7
- 230000000895 acaricidal effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 19
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- -1 chlorovinyl Chemical group 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 241000238876 Acari Species 0.000 claims description 3
- 241000607479 Yersinia pestis Species 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000000853 adhesive Substances 0.000 claims description 2
- 230000001070 adhesive effect Effects 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 5
- 230000000361 pesticidal effect Effects 0.000 claims 4
- 239000000575 pesticide Substances 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000002270 dispersing agent Substances 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000002562 thickening agent Substances 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 239000000080 wetting agent Substances 0.000 claims 1
- 239000013543 active substance Substances 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000010410 dusting Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- ZHLKXBJTJHRTTE-UHFFFAOYSA-N Chlorobenside Chemical compound C1=CC(Cl)=CC=C1CSC1=CC=C(Cl)C=C1 ZHLKXBJTJHRTTE-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 101100536883 Legionella pneumophila subsp. pneumophila (strain Philadelphia 1 / ATCC 33152 / DSM 7513) thi5 gene Proteins 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000007182 Ochroma pyramidale Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 101100240664 Schizosaccharomyces pombe (strain 972 / ATCC 24843) nmt1 gene Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 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
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
Landscapes
- 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
and acaricldal preparations containing them The invention relates to aearicidal preparat ons containing them and to a method of combating pests of the order The present invention provides the use of compounds of the general formula I for combating members of the order wherein R represents a cyclohexyl or cyclopentyl represents a hydrogen an alkyl or alkenyl residue having at most 4 carbon atoms which is optionally or an alkynyl residue having at most 4 carbon atoms or a phenyl residue which is optionally substituted by one or more halogen atoms or a nitro and represents a hydrogen atom or a methyl These active substances may be manufactured by reaction of a compound of formula II with a second compound of formula III R wherein Rg and the given and each represents a or a nitro and wherein one of the Y and Z represents a halogen especially chlorine or and the other an OH group which can also in the form of an alkali alcoholate or alkaline earth optionally in the presence of an agent which binds hydrogen and with subsequent of the resulting other in the case where represent a hydrogen The compounds of the invention are outstandingly suitable for combating pests of the order Acarina mites and spinning including also those showing resistance towards phosphoric acid The compounds also have a chemosterilising As an especially active there should be mentioned those compounds of formula I in which represents a butyl or butyl represents a hydrogen atom or a chlorovinyl or ethynyl group and represents a hydrogen atom or a methyl The invention also provides new compounds of formula and their indicated use in which formula R represents a cyclohexyl or cyclopentyl represents a alkyl or alkenyl residue or unsubstituted alkenyl residue having at most 4 carbon atoms or a phenyl residue which is optionally substituted by halogen or and represents a hydrogen atom or a methyl The invention further relates to compositions which contain these new compounds of formula together with a for one or more of the following dispersing wetting adhesives or In the substances can be in a liquid or solid in dry or in the form of wettable powders or dusting or through gas phase These methods are described in detail in Patent or British Patent or Swiss Patent In many cases the use of granules for the uniform release of active substances over a prolonged period of time is of These granules can be manufactured by dissolving the active substance in an organic absorption or adsorption of this solution by a mineral or polymer adsorbent material and removal of the They can also be manufactured by mixing the active substances of formula I with polymeri3able which a merisation is carried which leaves the active substances with the granulation carried out whilst the is still In order to dusting agents and ing such for for combating mites in it is possible to use calcium but also cork wood flour and other materials of vegetable origin as solid The various forms in which the active substances of the present invention can be used can be provided in the usual manner with addition of substances which improve the the the rain resistance or the trating amongst these there may be mentioned fatty casein or The agents according to the invention can be used by themselves or together with customary biocidcs for combating especially with fungicides or The concentration of the agents employed can vary within wide limits depending on the nature of the It is in general per cent by weight to 20 per cent by for more dilute whilst more concentrated agents contain 20 per cent by weight to 98 per cent by of active Very highly concentrated preparations be used in the ULV technique with minimal amounts of ULV technique is used with extremely finely atomising spray preferably the aid of In combating representatives of the order the following can especially be amongst the range of for use with the active tances of formula Chlorobenside Pluorobenside phonate propanecarboxylic acid and The following Examples illustrate In the two manufacturing Examples which the parts denote parts by weigh E x a p l e 1 240 parts of are dissolved in 1000 parts by volume of and mixed with 180 parts of potassium carbonate and 10 parts of dered potassium After one hour 140 parts of pargyl bromide are added and the mixture heated for hours under After dilution with ice the reaction product is taken up in ether which is washed with dilute sodium hydroxide solution and After evaporation of the ether the end product remains and is recrystallised from ethanol with the addition of ligroin point p 2 Manufacture of the of 4J A consisting of 45 parts of 85 potassium 30 parts of water and 100 parts of alcohol is added dropwise at whilst to 130 parts of in 100 parts of allyl After two hours the mixture is poured onto ice and the end product recrystallised from melting to The following compounds of formula IV can manufactured in the same manner as described in one of 1 or TABLE I Physical 24 cyclohexyl 25 cyclohexyl 3 26 cyclohexyl 27 29 sec 31 cyclohexyl 33 cyclohexyl 34 35 3 36 isopropyl H 37 isopropyl 3 38 39 40 41 cyclohexyl 42 3 butyl 44 46 47 isopropyl 48 isopropyl 51 Equal parts of an active substance according to the invention and precipitated silica are finely Dusting preferably containing of active can be ctured therefrom by mixing with kaolin or In order to manufacture a spraying the following coiponents are for example mixed and finely 50 parts of active substance according to the invention 20 ts of adsorbent 25 arts of Bolus alba kaolin parts of Easily soluble active substances can also be formulated as an emulsion concentrate according to the following 20 parts of active substance 70 parts of xylene 10 of a mixture of a reaction product of an phenol with ethylene oxide and calcium are On dilution with water the desired centration a sprayable is Granules g of one of the active substances of formula I are dissolved in 100 ml of acetone and the acetone solution thus obtained is poured over 92 g of granulated Attapulgite The whole is well mixed and the solvent is stripped in a rotary containing of active substance are E x a p 1 e against spider Bush plants in the leaf stage are infected 12 hours before treatment with the active by placing attacked pieces of leaf from a culture on the so that after thi3 time a population in all stages of development is present on the The plants are then sprayed with the e fied active substance with the aid of a chromatography iser until a uniform de osit of dro lets is leaf After 2 and the results are the parts of the plant are inspected under a scope in order to calculate the mortality percentages action on eggs is not ascertainable after 2 days with this since the average hatching is not yet accurately known at this point in The Table which follows gives the mortality percentages of the normally sensitive variety Koch and the mortality percentages of the phosphoric acid variety telarius Compound 9 serves as the active Action a ainst TABLE II M o r t a y after 2 days after 7 days introduced into a glass tube and dipped for 1 to 2 in 2 ml of an aqueous emulsion of series of 5 and 1 ppm of test after the test solution is removed and the container closed with a cotton wool After days 100 mortality found at the following limiting Compound 5 ppm Compound 10 ppm Compound 8 10 ppm insufficientOCRQuality
Claims (11)
1. A method of combating pests of the order Acarina which comprises applying thereto or to the habitat thereof a compound of the general formula I wherein R^ represents a methyl, isopropyl, sec. butyl, tert. butyl, cyclohexyl or cyclopentyl residue, represents a hydrogen atom, an optionally halogen-substituted alkyl or alkenyl residue having at most carbon atoms or an alkynyl. residue having at most carbon atoms or a phenyl residue which is optionally substituted by one or more halogen atoms or a nitro group, and represents a hydrogen atom or a methyl group.
2. A method as claimed in claim 1, wherein the active ingredient is a compound of the formula la wherein R^ represents a methyl, isopropyl, sec butyl, tert. butyl, cyclohexyl or cyclopentyl residue, R'2 represents a halogen-substituted alkyl or alkenyl residue or unsubstituted alkenyl residue having at most carbon atoms or a phenyl residue which is optionally substituted by halogen or nitro, and R-^ is a hydrogen atom or a methyl group. 33455-2
3. A method as claimed in claim 1, wherein in the compounds of the formula I R^ represents a methyl, isopropjrl, sec. butyl or tert. butyl residue, Rg represents a hydrogen atom or a methyl group, vinyl, chlorovinyl or ethynyl group, and R^ represents a hydrogen atom or a methyl group.
4. A method as claimed in claim 1, wherein the active ingredient is a compound as described in Example 1 or 2 or in Table I herein.
5. A method as claimed in claim 1, wherein the active ingredient is a compound of the formula
6. A pesticidal preparation which comprises as active ingredient a compound of the formula la as defined in claim 2, together with a carrier.
7. A pesticidal preparation, which comprises as active ingredient the compound of the formula given in claim 5, together with a carrier.
8. A pesticidal preparation as claimed in claim 6 or 7> wherein the carrier is a solvent, diluent, dispersing agent, emulsifierjf, wetting agent, adhesive or thickener or a futher pesticide.
9. · A pesticidal preparation as claimed in claim 8, 83455- wherein the further pesticide is N' - (4-chloro-2-methylphenyl) Ν,Ν-dimethylformamidine.
10. A compound of the formula la as defined in claim 2.
11. A compound of the formula
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1819968 | 1968-12-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL33455A0 IL33455A0 (en) | 1970-01-29 |
| IL33455A true IL33455A (en) | 1972-10-29 |
Family
ID=4431218
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL33455A IL33455A (en) | 1968-12-05 | 1969-11-28 | 2,4-dinitro-6-alkylphenyl-ethers and acaricidal preparations containing them |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE742623A (en) |
| BR (1) | BR6914795D0 (en) |
| CS (1) | CS158258B2 (en) |
| DE (1) | DE1959290A1 (en) |
| FR (1) | FR2025376A1 (en) |
| GB (1) | GB1279874A (en) |
| IE (1) | IE33664B1 (en) |
| IL (1) | IL33455A (en) |
| NL (1) | NL6918265A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS562901A (en) | 1979-06-19 | 1981-01-13 | Kaken Pharmaceut Co Ltd | Herbicide |
-
1969
- 1969-11-25 FR FR6940611A patent/FR2025376A1/fr not_active Withdrawn
- 1969-11-26 DE DE19691959290 patent/DE1959290A1/en active Pending
- 1969-11-28 IL IL33455A patent/IL33455A/en unknown
- 1969-12-04 NL NL6918265A patent/NL6918265A/xx unknown
- 1969-12-04 IE IE1634/69A patent/IE33664B1/en unknown
- 1969-12-04 BE BE742623D patent/BE742623A/xx unknown
- 1969-12-05 CS CS800969A patent/CS158258B2/cs unknown
- 1969-12-05 GB GB59610/69A patent/GB1279874A/en not_active Expired
- 1969-12-05 BR BR214795/69A patent/BR6914795D0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2025376A1 (en) | 1970-09-11 |
| BE742623A (en) | 1970-06-04 |
| DE1959290A1 (en) | 1970-07-09 |
| GB1279874A (en) | 1972-06-28 |
| CS158258B2 (en) | 1974-10-15 |
| NL6918265A (en) | 1970-06-09 |
| IL33455A0 (en) | 1970-01-29 |
| BR6914795D0 (en) | 1973-02-20 |
| IE33664B1 (en) | 1974-09-18 |
| IE33664L (en) | 1970-06-05 |
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