WO1993003617A1 - Composition insecticide - Google Patents
Composition insecticide Download PDFInfo
- Publication number
- WO1993003617A1 WO1993003617A1 PCT/JP1992/001070 JP9201070W WO9303617A1 WO 1993003617 A1 WO1993003617 A1 WO 1993003617A1 JP 9201070 W JP9201070 W JP 9201070W WO 9303617 A1 WO9303617 A1 WO 9303617A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- optionally substituted
- parts
- insecticidal
- insecticidal composition
- Prior art date
Links
- 230000000749 insecticidal effect Effects 0.000 title claims abstract description 21
- 239000000203 mixture Substances 0.000 title claims abstract description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 4
- 239000004480 active ingredient Substances 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 13
- -1 methylenedioxyphenyl group Chemical group 0.000 abstract description 12
- 239000004615 ingredient Substances 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000005412 pyrazyl group Chemical group 0.000 abstract 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- WABPPBHOPMUJHV-UHFFFAOYSA-N Sesamex Chemical compound CCOCCOCCOC(C)OC1=CC=C2OCOC2=C1 WABPPBHOPMUJHV-UHFFFAOYSA-N 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- 238000003958 fumigation Methods 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- PEYUIKBAABKQKQ-AFHBHXEDSA-N (+)-sesamin Chemical compound C1=C2OCOC2=CC([C@H]2OC[C@H]3[C@@H]2CO[C@@H]3C2=CC=C3OCOC3=C2)=C1 PEYUIKBAABKQKQ-AFHBHXEDSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 241001414720 Cicadellidae Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000238558 Eucarida Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241000254152 Sitophilus oryzae Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 229910052586 apatite Inorganic materials 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- PEYUIKBAABKQKQ-UHFFFAOYSA-N epiasarinin Natural products C1=C2OCOC2=CC(C2OCC3C2COC3C2=CC=C3OCOC3=C2)=C1 PEYUIKBAABKQKQ-UHFFFAOYSA-N 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000002316 fumigant Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940040145 liniment Drugs 0.000 description 1
- 239000000865 liniment Substances 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- VRMHCMWQHAXTOR-CMOCDZPBSA-N sesamin Natural products C1=C2OCOC2=CC([C@@H]2OC[C@@]3(C)[C@H](C=4C=C5OCOC5=CC=4)OC[C@]32C)=C1 VRMHCMWQHAXTOR-CMOCDZPBSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
-
- 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
- A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
Definitions
- the present invention relates to a novel insecticidal composition having an excellent insecticidal effect, comprising a combination of an amide derivative of the following formula [I] and a synergist having a methylenedioxyphenyl group.
- the present inventor studied a more effective use of the amine derivative represented by the following formula [I] and studied a combination with a synergist having a methylenedioxyphenyl group. It has been found that a powerful insecticidal effect can be obtained.
- the present invention has the general formula (I)
- R is an optionally substituted pyridyl group, virazyl group, or thiazolyl group, excluding an unsubstituted 2-pyridyl group
- R 2 is a hydrogen atom
- an optionally substituted R 3 represents a hydrogen atom, a substituted or unsubstituted alkyl group, and represents a cyano group or a nitro group.
- a salt thereof and a synergist having a methylenedioxyphenyl group It has been found that a novel active substance combination exhibits an excellent insecticidal effect.
- Amin derivatives alone are used to control the insects such as aphid, leafhopper, rice weevil, brown beetle, fruit tree, vegetables, etc. It is more effective than usual and shows a synergistic insecticidal effect.
- Preferred amide derivatives of the general formula [I] used in the insecticidal composition according to the present invention are defined as follows. .
- R is a pyridyl group, a virazinyl group or a thiazolyl group which may be substituted with a halogen atom such as a chloro atom, excluding an unsubstituted 2-pyridyl group;
- R 2 is a hydrogen atom;
- R 3 represents a hydrogen atom, an alkyl group, and represents a Shimano group or a nitro group.
- Examples of the amide derivative of the general formula [I] used in the insecticidal composition according to the present invention include the compounds shown in Table 1 below. Method for producing the amine derivative or salt thereof The methods and their use as insecticides are described in WO 91/04965 in the P Table 1
- synergists having a methylenedioxyphenyl group used in the present invention include the compounds shown in Table 2. Common name structure
- the weight ratio of the active substance in each group in the active substance is generally the same as that of the active substance in the active substance group of the amide derivative of the general formula [I] or a salt thereof.
- 1 to 20 parts by weight of the agent can be used.
- the insecticidal composition according to the present invention exhibits an excellent insecticidal effect, and is applied by spraying, top dressing, underwater application, water surface application, soil surface application, soil mixing treatment, planting hole treatment, seedling immersion, seed disinfection, seedling raising box It can be used for application, smoking, fumigation, application, bait etc.
- the insecticidal composition according to the present invention exhibits a stronger insecticidal effect than when each active compound is applied alone, so that it has no phytotoxicity to crops, has low toxicity to mixed-breed animals, and can be used safely.
- the insecticidal composition of the present invention comprises a compound represented by the general formula [I] and methylenedioxy. It contains a synergist having a fluorine group as an active ingredient, and can be used as it is as a pure product of the active ingredient compound. Water solvent, powder, emulsion, oil, granule, flowable, fumigation, fumigant, aerosol, liniment, bait, etc. Those prepared separately may be used as a mixture. Additives and carriers include solid powders, such as soy flour and flour, vegetable powders, diatomaceous earth, apatite, gypsum, talc, bentonite, clay, and other mineral powders, sodium benzoate, urea, and the like. Organic and inorganic compounds such as sodium sulfate are used.
- liquid dosage form uses vegetable oil, mineral oil, petroleum fractions such as kerosene, xylene and sorbent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, trichloroethylene, methylisobutyl Use ketone and water as solvents.
- a surfactant can be added if necessary to obtain a uniform and stable form.
- the wettable powder, emulsion, aqueous solvent, flowable, etc. thus obtained is diluted with water to a predetermined concentration to form a suspension or emulsion, and the oils, powders, and granules are sprayed as they are. Used in.
- Example 2 wettable powder 10 parts of the active compound of the formula (I)
- Test Example 1 Test on housefly Absorbent cotton was placed in a small petri dish having a diameter of 3 cm, and an aqueous solution of sugar having a predetermined concentration of a wettable powder according to the example was dropped, and used as poison bait. This petri dish was placed in a high petri dish and inoculated with 10 housefly adults. They were covered with a wire mesh and placed in a thermostatic chamber at a temperature of 25 ° C and a humidity of 65%, and the insecticidal rate was examined two days later. Table 3 shows the results.
- a cabbage leaf piece was added to an aqueous solution of a drug diluted to a predetermined concentration of a wettable powder according to Example 2. 170
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)
Abstract
L'invention se rapporte à une composition insecticide qui contient comme ingrédients actifs un composé représenté par la formule générale (I) ou un sel de ce composé, ainsi qu'un agent augmentant la synergie comportant un groupe méthylène-dioxyphényle. Dans la formule (I), R1 représente pyridyle éventuellement subtitué, pyrazyle ou thiazolyle, à l'exception de 2-pyridyle non substitué; R2 représente hydrogène, alkyle éventuellement substitué, cycloalkyle ou alcoxy; R3 représente hydrogène ou alkyle éventuellement substitué; et R4 représente cyano ou nitro. Cette composition a un effet insecticide plus grand que celui de l'ingrédient utilisé seul, de sorte que la synergie de la composition est excellente.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3/238925 | 1991-08-27 | ||
| JP3238925A JPH0558811A (ja) | 1991-08-27 | 1991-08-27 | 殺虫組成物 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1993003617A1 true WO1993003617A1 (fr) | 1993-03-04 |
Family
ID=17037319
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP1992/001070 WO1993003617A1 (fr) | 1991-08-27 | 1992-08-25 | Composition insecticide |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPH0558811A (fr) |
| WO (1) | WO1993003617A1 (fr) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996003879A1 (fr) * | 1994-07-29 | 1996-02-15 | Bayer Aktiengesellschaft | Insecticides |
| EP0617890B1 (fr) * | 1993-03-18 | 1998-11-18 | Nihon Bayer Agrochem K.K. | Compositions insecticides synergiques |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006298767A (ja) * | 2005-04-15 | 2006-11-02 | Sumitomo Chemical Co Ltd | ハエ亜目害虫防除剤 |
| ITMI20050729A1 (it) * | 2005-04-22 | 2006-10-23 | Endura Spa | Nuova formulazione biologicamente attiva |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991004965A1 (fr) * | 1989-10-06 | 1991-04-18 | Nippon Soda Co., Ltd. | Derives d'amine |
-
1991
- 1991-08-27 JP JP3238925A patent/JPH0558811A/ja active Pending
-
1992
- 1992-08-25 WO PCT/JP1992/001070 patent/WO1993003617A1/fr active Application Filing
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991004965A1 (fr) * | 1989-10-06 | 1991-04-18 | Nippon Soda Co., Ltd. | Derives d'amine |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0617890B1 (fr) * | 1993-03-18 | 1998-11-18 | Nihon Bayer Agrochem K.K. | Compositions insecticides synergiques |
| WO1996003879A1 (fr) * | 1994-07-29 | 1996-02-15 | Bayer Aktiengesellschaft | Insecticides |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0558811A (ja) | 1993-03-09 |
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