US3646212A - Miticides comprising an ester of 4 6-dinitro-2-sec. butyl-phenol and 2 4 5 4'-tetrachlorodiphenyl sulfide or sulfone - Google Patents
Miticides comprising an ester of 4 6-dinitro-2-sec. butyl-phenol and 2 4 5 4'-tetrachlorodiphenyl sulfide or sulfone Download PDFInfo
- Publication number
- US3646212A US3646212A US845912A US3646212DA US3646212A US 3646212 A US3646212 A US 3646212A US 845912 A US845912 A US 845912A US 3646212D A US3646212D A US 3646212DA US 3646212 A US3646212 A US 3646212A
- Authority
- US
- United States
- Prior art keywords
- sec
- dinitro
- sulfone
- tetrachlorodiphenyl
- tetrasul
- 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 - Lifetime
Links
- 150000003457 sulfones Chemical class 0.000 title abstract description 4
- 150000002148 esters Chemical class 0.000 title description 2
- 239000000642 acaricide Substances 0.000 title 1
- QUWSDLYBOVGOCW-UHFFFAOYSA-N Tetrasul Chemical compound C1=CC(Cl)=CC=C1SC1=CC(Cl)=C(Cl)C=C1Cl QUWSDLYBOVGOCW-UHFFFAOYSA-N 0.000 abstract description 17
- 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 abstract description 14
- 239000000203 mixture Substances 0.000 abstract description 11
- 241001454295 Tetranychidae Species 0.000 abstract description 8
- HDWLUGYOLUHEMN-UHFFFAOYSA-N Dinobuton Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)OC(C)C HDWLUGYOLUHEMN-UHFFFAOYSA-N 0.000 abstract description 7
- ZRDUSMYWDRPZRM-UHFFFAOYSA-N 2-sec-butyl-4,6-dinitrophenyl 3-methylbut-2-enoate Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)C=C(C)C ZRDUSMYWDRPZRM-UHFFFAOYSA-N 0.000 abstract description 6
- 230000002195 synergetic effect Effects 0.000 abstract description 4
- HKDUMDQZYRXNGQ-UHFFFAOYSA-N (2-butylphenyl) octadecanoate Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)OC1=C(C=CC=C1)CCCC HKDUMDQZYRXNGQ-UHFFFAOYSA-N 0.000 abstract description 3
- ZIXSUNDDJYAXKV-UHFFFAOYSA-N (2-butylphenyl) propan-2-yl carbonate Chemical compound C(OC1=C(C=CC=C1)CCCC)(OC(C)C)=O ZIXSUNDDJYAXKV-UHFFFAOYSA-N 0.000 abstract description 3
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical class CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 abstract description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 2
- 230000000361 pesticidal effect Effects 0.000 abstract description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 description 14
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 description 10
- -1 butyl-phenyl esters Chemical class 0.000 description 9
- 239000007921 spray Substances 0.000 description 8
- 239000004495 emulsifiable concentrate Substances 0.000 description 5
- 239000000080 wetting agent Substances 0.000 description 5
- 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 4
- 244000141359 Malus pumila Species 0.000 description 4
- 235000011430 Malus pumila Nutrition 0.000 description 4
- 235000015103 Malus silvestris Nutrition 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000488583 Panonychus ulmi Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 230000003129 miticidal effect Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- AHIHJODVQGBOND-UHFFFAOYSA-M propan-2-yl carbonate Chemical compound CC(C)OC([O-])=O AHIHJODVQGBOND-UHFFFAOYSA-M 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- BQQUBTKVRLRBCA-UHFFFAOYSA-N (2-butylphenyl) 3-methylbut-2-enoate Chemical compound CCCCC1=CC=CC=C1OC(=O)C=C(C)C BQQUBTKVRLRBCA-UHFFFAOYSA-N 0.000 description 1
- QQGRFMIMXPWKPM-UHFFFAOYSA-N 2,3,4-tributylphenol Chemical class CCCCC1=CC=C(O)C(CCCC)=C1CCCC QQGRFMIMXPWKPM-UHFFFAOYSA-N 0.000 description 1
- GXJQMKFJQFGQKV-KHPPLWFESA-N 2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS(O)(=O)=O GXJQMKFJQFGQKV-KHPPLWFESA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 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
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([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])[H] 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- VDHOTNRNELFZCL-UHFFFAOYSA-M sodium;2,3-dimethylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(C)C(C)=CC2=C1 VDHOTNRNELFZCL-UHFFFAOYSA-M 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000011885 synergistic combination 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
Definitions
- the present invention relates to pesticides useful for controlling spider mites (tetranychidae).
- DNBP esters 4,6-dinitro-2-sec. butyl-phenyl esters (DNBP esters) to combat spider mites, for example DNBP dimethylacrylate (binapacryl), DNBP stearate, or DNBP isopropyl carbonate (dinobuton),
- the present invention provides agents for combating spider mites characterized by a content of a synergistic combination of DNBP dimethylacrylate (binapacryl), or DNBP stearate, or DNBP isopropyl carbonate (dinobuton) with 2,4,5,4'-tetrachlorodiphenyl sulfide (tetrasul) or 2, 4,5,4-tetrachlorodiphenyl sulfone (tetradifon).
- a ratio of the active ingredients of about 3 to 7 parts by weight of the DNBP ester to about 1 part by weight of tetrasul or tetradifon is preferred.
- the pests can be destroyed by a combination of the active ingredients according to the invention.
- the combinations of the active ingredients have a synergistic effect, especially on spider mites. The effect is illustrated in the following Example 3.
- the combinations according to the invention have a good effect on mildew (Erysiphaceen).
- the pesticides according to the invention are advantageously used in the form of an emulsifiable concentrate containing 10 to 70% by weight of the mixture of effective ingredients and 5 to by weight of a wetting agent, the remainder to 100% by weight being an organic solvent.
- the pesticides of the invention can also be used in the form of a Wettable powder or of a paste containing 10 to 80% by weight of the mixture of active ingredients and 3 to 10% by Weight of a wetting agent and/0r dispersing agent, the remainder to 100% by weight being one or several solid inert substances.
- Suitable wetting agents are, for example, ethoxylated alkyl phenols, ethoxylated oleyl or stearyl amines and United States Patent O 3,646,212 Patented Feb. 29, 1972 alkyl or alkyl-aryl sulfonates.
- Suitable dispersing agents are, for example, sodium lignin sulfonate, sodium 2,2- dinaphthylmethane 6,6 disulfonate, sodium dibutylnaphthalene-sulfonate or sodium oleylmethyltaurine.
- Suitable organic solvents are inert liquids such as butanol, cyclohexanone, dimethyl formamide, toluene, xylene or higher boiling aromatic hydrocarbons as well as ketones, for example methylethyl ketone, mehylisobutyl ketone or isophorone.
- mineral substances such as aluminum silicates, argillaceous earths, kaolin, kieselguhr or hydrated silicic acids.
- Suitable grinding auxiliaries are inorganic or organic salts such as sodium sulfate, ammonium sulfate, sodium carbonate, sodium bicarbonate, sodium thiosulfate, sodium stearate or sodium acetate.
- EXAMPLE 1 Wettable powders having a content of active ingredients of 4 parts of DNBP ester and 1 part of tetrasul or tetradifon were obtained by mixing:
- Emulsifiable concentrates having a content of active ingredients of 3 parts of the DNBP esters specified in Example 1 and 1 part of tetrasul or tetradifon are obtained by mixing:
- EXAMPLE 3 Small apple trees in pots were infested with fruit tree red spiders (Metatetranyclzus ulmi) of the strain Dardar. The trees were kept in the greenhouse until a complete population had grown on the leaves, i.e. a great number of eggs, larvae, nymphs and imagoes. A few of the trees were sprayed With aqueous spray liquors of the combinations according to the invention in the form of emulsions made with the emulsifiable concentrates specified in Example 2. The combinations contained the active ingredients in a ratio of 3:1.
- Example 2 In the manner described in Example 2 further combinations were prepared containing 35 parts of one of the indicated DNBP esters and 5 parts of tetrasul or tetradifon. In these combinations the active ingredients were contained in a ratio of 7:1. Further apple trees were treated with aqueous spray liquors made from the corresponding emulsifiable concentrates.
- a miticidal composition comprising as the effective ingredient thereof a mixture of from about 3 to 7 parts by Weight of an ester of 4,6-dinitro-2-sec. butylphenol selected from the group consisting of the dimethylacrylate, stearate, and isopropyl carbonate With 1 part by Weight of a member selected from the group consisting of 2,4,5,4'- tetrachlorodiphenyl sulfide and 2,4,5,4'-tetrachlorodiphenyl sulfone.
- miticidal composition of claim 1 in the form of an emulsifiable concentrate comprising 10 to percent of said effective ingredient and 5 to 15 percent of a wetting agent, by weight of said composition, in an organic solvent.
- the miticidal composition of claim 1 in the form of a Wettable powder comprising 10 to percent of said efiective ingredient and 3 to 10 percent of at least one member selected from the group consisting of wetting agents and dispersing agents, by weight of said composition, in admixture with an inert solid.
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681792281 DE1792281A1 (de) | 1968-08-14 | 1968-08-14 | Mittel zur Bekaempfung von Spinnmilben |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3646212A true US3646212A (en) | 1972-02-29 |
Family
ID=5707347
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US845912A Expired - Lifetime US3646212A (en) | 1968-08-14 | 1969-07-29 | Miticides comprising an ester of 4 6-dinitro-2-sec. butyl-phenol and 2 4 5 4'-tetrachlorodiphenyl sulfide or sulfone |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3646212A (https=) |
| AT (1) | AT298878B (https=) |
| BE (1) | BE737506A (https=) |
| CH (1) | CH513582A (https=) |
| DE (1) | DE1792281A1 (https=) |
| DK (1) | DK121106B (https=) |
| ES (1) | ES370456A1 (https=) |
| FR (1) | FR2015636A1 (https=) |
| GB (1) | GB1267253A (https=) |
| IL (1) | IL32734A (https=) |
| NL (1) | NL6911907A (https=) |
| RO (1) | RO60066A (https=) |
| SE (1) | SE349733B (https=) |
-
1968
- 1968-08-14 DE DE19681792281 patent/DE1792281A1/de active Pending
-
1969
- 1969-07-28 RO RO60642A patent/RO60066A/ro unknown
- 1969-07-29 US US845912A patent/US3646212A/en not_active Expired - Lifetime
- 1969-07-30 IL IL32734A patent/IL32734A/xx unknown
- 1969-08-05 NL NL6911907A patent/NL6911907A/xx unknown
- 1969-08-12 FR FR6927683A patent/FR2015636A1/fr not_active Withdrawn
- 1969-08-12 ES ES370456A patent/ES370456A1/es not_active Expired
- 1969-08-12 SE SE11185/69A patent/SE349733B/xx unknown
- 1969-08-12 AT AT775869A patent/AT298878B/de active
- 1969-08-12 CH CH1223069A patent/CH513582A/de not_active IP Right Cessation
- 1969-08-13 DK DK435069AA patent/DK121106B/da unknown
- 1969-08-14 GB GB1267253D patent/GB1267253A/en not_active Expired
- 1969-08-14 BE BE737506D patent/BE737506A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE349733B (https=) | 1972-10-09 |
| NL6911907A (https=) | 1970-02-17 |
| IL32734A (en) | 1972-11-28 |
| ES370456A1 (es) | 1971-04-16 |
| CH513582A (de) | 1971-10-15 |
| BE737506A (https=) | 1970-02-16 |
| DE1792281A1 (de) | 1971-10-28 |
| AT298878B (de) | 1972-05-25 |
| GB1267253A (https=) | 1972-03-15 |
| FR2015636A1 (https=) | 1970-04-30 |
| RO60066A (https=) | 1976-10-15 |
| IL32734A0 (en) | 1969-09-25 |
| DK121106B (da) | 1971-09-06 |
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