WO1996032842A1 - Protection of crops against birds using a compound of phenylpyrazole type - Google Patents
Protection of crops against birds using a compound of phenylpyrazole type Download PDFInfo
- Publication number
- WO1996032842A1 WO1996032842A1 PCT/EP1996/001625 EP9601625W WO9632842A1 WO 1996032842 A1 WO1996032842 A1 WO 1996032842A1 EP 9601625 W EP9601625 W EP 9601625W WO 9632842 A1 WO9632842 A1 WO 9632842A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- birds
- active material
- application
- frequented
- crop
- Prior art date
Links
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
- A01N47/02—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 no bond to a nitrogen atom
-
- 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
Definitions
- the present invention relates to a new process for repelling birds and to a new process for protecting crops against birds.
- the seed of a cereal is devoid of its nutrient substance and is therefore no longer capable of being of interest to a bird in search of food, ⁇ good repellent must therefore exert its effect for a period sufficient to enable the cereal to reach this stage of development.
- An object of the present invention is to provide a new process for the protection of crops against birds.
- Another object of the present invention is to provide a process for the protection of crops against birds which has none or few of the disadvantages of known repellents and which corresponds, in all or part, to the quality objectives required for an ideal repellent.
- Another object of the present invention is to provide a process for the protection of crops against harmful birds and against harmful insects si ultaneously.
- Another object of the present invention is to provide a new process for repelling birds.
- Another object of the present invention is to provide new compositions which are repellent with respect to birds.
- compositions comprising, as bird-repellent active material, 1-phenylpyrazoles and preferably 1-phenylpyrazoles of general formula (I) .
- R x is CM or methyl
- R 2 is S (0) a R 3 ;
- R 3 is alkyl or haloalkyl
- R 4 represents a hydrogen or halogen atom or an
- R 5 and R ( independently represent the hydrogen atom or an alkyl, haloalkyl, C(0)alkyl or S(0) r CF 3 radical; or R s and R c can together form a divalent alkylene radical which can be interrupted by one or two divalent heteroatoms, such as oxygen or sulphur;
- R 7 represents an alkyl or haloalkyl radical
- R a represents an alkyl or haloalkyl radical or a hydrogen atom
- R represents an alkyl radical or a hydrogen atom
- R 10 represents a phenyl or heteroaryl group which is optionally substituted by one or a number of halogen atoms or groups such as OH, -0-alkyl, -S-alkyl, ⁇ > ⁇ till ⁇ .
- R X1 and R 12 represent, independently of one another, a hydrogen or halogen atom
- R 13 represents a halogen atom or a haloalkyl, haloalkoxy, S(0) q CF 3 or SF S group; m, n, q, and r represent, independently of one another, an integer equal to 0, 1 or 2;
- X represents a trivalent nitrogen atom or a C-R 12 radical, the other three valencies of the carbon atom forming part of the aromatic ring; provided that, when R ⁇ is methyl, then R 3 is haloalkyl, R 4 is NH 2 , R n is Cl, R 13 is CF 3 and X is N.
- a preferred class of compounds of formula (I) is composed of the compounds such that - ⁇ is CN, and/or R 3 is haloalkyl, and/or R 4 is NH 2 , and/or R X1 and R 12 are, independently of one another, a halogen atom, and R 13 is haloalkyl.
- a compound of formula (I) which is very particularly preferred in the invention is l-[2,6-Cl 2 -4-CF j phenyl] -3-CN-4-[SO-CF,] -5-NH 2 pyrazole, hereinafter known as compound A.
- the 1-arylpyrazoles of the present invention are effective for repelling with respect to birds of various natures such as those mentioned above.
- Compounds of formula (I) can be prepared according to one or other of the processes described in Patent Applications WO 87/3781, 93/6089 or 94/21606 or European Patent Application 295,117, or any other process coming within the competence of the person skilled in the art who is a specialist in chemical synthesis.
- compositions described in the prior art were prepared for an insecticidal purpose.
- the formulations or compositions for repelling birds may be similar or may be adapted in order to make them still more suitable for their repellent use, in particular by additions of appropriate adjuvants.
- the formulations which are suitable for the employment of the process according to the invention contain from 0.0001 to 95 % by weight of active material of formula (I) .
- the concentrated formulations for commercial use for storage, sale or transportation
- the compositions as used by the applicator are generally much more dilute compositions.
- the compositions according to the invention contain various solid or liquid vehicles, surfactants and other adjuvants of the most varied natures but which are environmentally acceptable.
- the 1-arylpyrazoles employed in the invention can advantageously be formulated as fluid or liquid compositions, wettable powders or microemulsions. Such formulations generally comprise one or a number of solid or liquid inert vehicles or diluents which are agronomically acceptable.
- Wettable powder or concentrated granule formulations can be prepared by milling a 1-arylpyrazole of formula (I) with approximately 1 % to 20 % by weight of solid anionic surfactant.
- a suitable anionic surfactant is the dioctyl ester of the sodium salt of sulfosuccinic acid.
- Approximately 85 % to 95 % by weight of inert diluent, such as montmorillonite, attapulgite, limestone, talc, kaolin, diatomaceous earth, pumice, silicates or other similar products, can be included in such formulations, as well as the other adjuvants indicated above.
- pyrazole ⁇ which are used in the present invention have a low solubility but can be used at low doses. They can therefore be employed in solutions or emulsions or, preferably, in the form of aqueous or non-aqueous suspensions comprising the appropriate adjuvants and/or cosolvents. Acetone and methyl ether ketone can be used as cosolvents. Any liquid medium can be used, provided that it is neither toxic for plants nor for the environment.
- cosolvents and/or wetting or dispersing agents can be used.
- Other additives can also be employed, such as talc.
- Active materials of formula (I) can be absorbed onto vehicles, for example ver iculite, clay, talc, kaolin or others, in particular to form granules.
- the 1-arylpyrazoles are also effective in protecting seeds, as well as plantlet ⁇ or young seedlings or plants which are more advanced in maturity.
- the most varied crops can thus be protected, in particular wheat, maize, rice, barley, rye, beets and any plant which is sown or which passes through the plantlet stage.
- the application of the 1-arylpyrazoles according to the invention is often carried out in the form of granules over the plants or over the soil of the crop which has to be protected. These applications in the form of granules are generally carried out so as to provide a dose of active material of approximately 0.01 kg/ha to approximately 1 kg/ha of active material and preferably between 0.02 and 0.3 kg/ha.
- the 1-arylpyrazoles of the invention are also effective in protecting crops by application of the active material to the seed before sowing.
- the seed can be treated by coating or film coating or impregnation or immersion in a liquid or a pasty formulation known per se, followed by drying.
- the invention thus further comprises a process for the protection of crops against birds, characterized in that an effective amount of compound of general formula (I) is applied to the said crop or to the cultivated region comprising the said crop.
- This application to the crop can be carried out by application of a composition comprising the active material to the cultivated ground before sowing or after sowing.
- the invention is employed by application of an effective amount of compound of formula (I) to the seed which has to be sown.
- the invention thus further relates to the use of compounds of formula (I) as repellents with respect to birds.
- the invention thus further relates to seeds intended to be sown in a region frequented or capable of being frequented by birds, characterized in that they are treated with an active material or a composition as defined above.
- compositions intended to be distributed over a region frequented or capable of being frequented by birds characterized in that they comprise an active material as defined above.
- the sowing is carried out in a field frequented by pheasants.
- the amount of seed remaining in the field after 3 days is measured and the result observed is expressed in the form of a percentage by number with respect to the amount of seed sown. 72 % of the seed remains, instead of 23 % for untreated controls.
- Example 2 The procedure is the same as in Example 1, but with sunflower seeds. 96 % of the seeds remain, instead of 36 % for the untreated control.
- Example 3
- Example 2 The procedure is the same as in Example 1, but with a field frequented by crows. 96 % of the seeds remain, instead of 19 % for the untreated control.
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)
- Catching Or Destruction (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT96912020T ATE220293T1 (en) | 1995-04-19 | 1996-04-18 | PROTECTION OF CROPS AGAINST BIRD USING A COMPOUND OF THE PHENYLPYRAZOLE TYPE |
SI9630485T SI0821552T1 (en) | 1995-04-19 | 1996-04-18 | Protection of crops against birds using a compound of phenylpyrazole type |
DK96912020T DK0821552T3 (en) | 1995-04-19 | 1996-04-18 | Protection of beneficial plants against birds using a phenylpyrazole-type compound |
EP96912020A EP0821552B1 (en) | 1995-04-19 | 1996-04-18 | Protection of crops against birds using a compound of phenylpyrazole type |
US08/945,183 US6013661A (en) | 1995-04-19 | 1996-04-18 | Protection of crops against birds using a compound of phenylpyrazole type |
AU55009/96A AU5500996A (en) | 1995-04-19 | 1996-04-18 | Protection of crops against birds using a compound of phenyl pyrazole type |
DE69622272T DE69622272T2 (en) | 1995-04-19 | 1996-04-18 | PROTECTION OF CROP PLANTS AGAINST BIRD USING A PHENYLPYRAZOL TYPE COMPOUND |
JP8531470A JPH11503741A (en) | 1995-04-19 | 1996-04-18 | Protection of crops against birds using phenylpyrazole type compounds |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR95/04940 | 1995-04-19 | ||
FR9504940A FR2733120B1 (en) | 1995-04-19 | 1995-04-19 | PROTECTION OF CROPS AGAINST BIRDS USING A PHENYLPYRAZOLE COMPOUND |
Publications (2)
Publication Number | Publication Date |
---|---|
WO1996032842A1 true WO1996032842A1 (en) | 1996-10-24 |
WO1996032842A9 WO1996032842A9 (en) | 1997-06-05 |
Family
ID=9478429
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1996/001625 WO1996032842A1 (en) | 1995-04-19 | 1996-04-18 | Protection of crops against birds using a compound of phenylpyrazole type |
Country Status (19)
Country | Link |
---|---|
US (1) | US6013661A (en) |
EP (1) | EP0821552B1 (en) |
JP (1) | JPH11503741A (en) |
AR (1) | AR001640A1 (en) |
AT (1) | ATE220293T1 (en) |
AU (1) | AU5500996A (en) |
CA (1) | CA2218047A1 (en) |
CO (1) | CO4650119A1 (en) |
DE (1) | DE69622272T2 (en) |
DK (1) | DK0821552T3 (en) |
ES (1) | ES2175088T3 (en) |
FR (1) | FR2733120B1 (en) |
MY (1) | MY125644A (en) |
PE (1) | PE3198A1 (en) |
PT (1) | PT821552E (en) |
SI (1) | SI0821552T1 (en) |
TW (1) | TW360640B (en) |
WO (1) | WO1996032842A1 (en) |
ZA (1) | ZA963143B (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE59611362D1 (en) * | 1995-09-19 | 2006-08-17 | Bayer Bioscience Gmbh | PLANTS SYNTHETIZING A MODIFIED STARCH, PROCESS FOR THEIR MANUFACTURE AND MODIFIED STARCH |
FR3140472A1 (en) | 2022-10-03 | 2024-04-05 | Acoudesign | DEVICE FOR GENERATION OF ACOUSTIC AND/OR VIBRATORY WAVES ON A FLEXIBLE STRUCTURE |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0295117A1 (en) * | 1987-06-12 | 1988-12-14 | Rhone-Poulenc Agriculture Limited | Derivatives of N-phenylpyrazoles |
EP0500209A1 (en) * | 1991-01-18 | 1992-08-26 | Rhone-Poulenc Agrochimie | Pesticidal 1-(2-pyridyl)pyrazoles |
WO1993006089A1 (en) * | 1991-09-27 | 1993-04-01 | Zeneca Limited | N-phenylphrazoles as insecticides and acaricides |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3602728A1 (en) * | 1985-05-17 | 1986-11-20 | Bayer Ag, 51373 Leverkusen | PEST CONTROL AGAINST PYRAZOLE DERIVATIVES |
GB8531485D0 (en) * | 1985-12-20 | 1986-02-05 | May & Baker Ltd | Compositions of matter |
US5232940A (en) * | 1985-12-20 | 1993-08-03 | Hatton Leslie R | Derivatives of N-phenylpyrazoles |
WO1992009196A1 (en) * | 1990-11-29 | 1992-06-11 | Osaka Gas Company Limited | Animal repellent material |
FR2696906B1 (en) * | 1992-10-20 | 1996-09-20 | Rhone Poulenc Agrochimie | PROCESS FOR THE AGROCHEMICAL TREATMENT OF RICE AND SEEDS THUS PROCESSED. |
GB9306184D0 (en) * | 1993-03-25 | 1993-05-19 | Zeneca Ltd | Heteroaromatic compounds |
-
1995
- 1995-04-19 FR FR9504940A patent/FR2733120B1/en not_active Expired - Lifetime
-
1996
- 1996-04-12 TW TW085104354A patent/TW360640B/en active
- 1996-04-17 AR AR33619296A patent/AR001640A1/en unknown
- 1996-04-18 MY MYPI96001482A patent/MY125644A/en unknown
- 1996-04-18 US US08/945,183 patent/US6013661A/en not_active Expired - Fee Related
- 1996-04-18 DK DK96912020T patent/DK0821552T3/en active
- 1996-04-18 CO CO96018739A patent/CO4650119A1/en unknown
- 1996-04-18 PE PE1996000268A patent/PE3198A1/en not_active Application Discontinuation
- 1996-04-18 EP EP96912020A patent/EP0821552B1/en not_active Expired - Lifetime
- 1996-04-18 PT PT96912020T patent/PT821552E/en unknown
- 1996-04-18 DE DE69622272T patent/DE69622272T2/en not_active Expired - Fee Related
- 1996-04-18 SI SI9630485T patent/SI0821552T1/en unknown
- 1996-04-18 WO PCT/EP1996/001625 patent/WO1996032842A1/en active IP Right Grant
- 1996-04-18 JP JP8531470A patent/JPH11503741A/en not_active Ceased
- 1996-04-18 ES ES96912020T patent/ES2175088T3/en not_active Expired - Lifetime
- 1996-04-18 AT AT96912020T patent/ATE220293T1/en not_active IP Right Cessation
- 1996-04-18 AU AU55009/96A patent/AU5500996A/en not_active Abandoned
- 1996-04-18 CA CA002218047A patent/CA2218047A1/en not_active Abandoned
- 1996-04-19 ZA ZA9603143A patent/ZA963143B/en unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0295117A1 (en) * | 1987-06-12 | 1988-12-14 | Rhone-Poulenc Agriculture Limited | Derivatives of N-phenylpyrazoles |
EP0500209A1 (en) * | 1991-01-18 | 1992-08-26 | Rhone-Poulenc Agrochimie | Pesticidal 1-(2-pyridyl)pyrazoles |
WO1993006089A1 (en) * | 1991-09-27 | 1993-04-01 | Zeneca Limited | N-phenylphrazoles as insecticides and acaricides |
Also Published As
Publication number | Publication date |
---|---|
PT821552E (en) | 2002-10-31 |
CA2218047A1 (en) | 1996-10-24 |
DE69622272D1 (en) | 2002-08-14 |
TW360640B (en) | 1999-06-11 |
PE3198A1 (en) | 1998-02-21 |
US6013661A (en) | 2000-01-11 |
SI0821552T1 (en) | 2002-10-31 |
EP0821552B1 (en) | 2002-07-10 |
FR2733120B1 (en) | 2002-09-13 |
ES2175088T3 (en) | 2002-11-16 |
CO4650119A1 (en) | 1998-09-03 |
ATE220293T1 (en) | 2002-07-15 |
DK0821552T3 (en) | 2002-11-04 |
JPH11503741A (en) | 1999-03-30 |
AR001640A1 (en) | 1997-11-26 |
MY125644A (en) | 2006-08-30 |
ZA963143B (en) | 1997-02-28 |
AU5500996A (en) | 1996-11-07 |
DE69622272T2 (en) | 2003-01-16 |
FR2733120A1 (en) | 1996-10-25 |
EP0821552A1 (en) | 1998-02-04 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4578506B2 (en) | Use of N-arylpyrazole or N-heteroarylpyrazole compounds for regulating plant growth | |
KR100428231B1 (en) | Control of light moth grass by 1-arylpyrazole or 1-heteroarylpyrazole compound | |
EP0821552B1 (en) | Protection of crops against birds using a compound of phenylpyrazole type | |
US5500437A (en) | Microbicides | |
JP2832482B2 (en) | Insecticidal fungicide composition | |
WO1996032842A9 (en) | Protection of crops against birds using a compound of phenylpyrazole type | |
JP2884425B2 (en) | Insecticidal composition for agricultural use | |
JPS6368505A (en) | Agricultural, insecticidal and germicidal composition | |
JPH05112405A (en) | Insecticidal composition | |
US5977156A (en) | Fungicidal pyrazoles | |
JP2003055115A (en) | Insecticidal and fungicidal mix composition for paddy rice | |
KR100478401B1 (en) | Fungicidal and insecticidal compositions | |
JPS6372610A (en) | Insecticidal and fungicidal composition for agricultural use | |
JPH01186849A (en) | Diphenylamine derivative, production thereof and harmful organism controller comprising said derivative as active ingredient | |
JPH072607B2 (en) | Agricultural insecticidal bactericidal composition | |
JPH0784363B2 (en) | Insecticidal germicidal composition for agriculture | |
WO1997035481A1 (en) | Herbicidal composition | |
JPH0558401B2 (en) | ||
US5585329A (en) | Plant growth promotion using 3-cyano-1-phenylpyrazoles such as fipronil | |
EP0111413B1 (en) | Novel sulfone, process for its preparation, composition containing it and use thereof | |
USH1900H (en) | Method of combating insect eggs | |
US4132785A (en) | Isopropyl parathion as an insecticide for treating soil | |
JPH04275201A (en) | Herbicide composition | |
JP2814679B2 (en) | Agricultural and horticultural fungicides | |
JPS6351304A (en) | Herbicide composition |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AL AM AU BB BG BR CA CN CZ EE GE HU IS JP KG KP KR LK LR LT LV MD MG MK MN MX NO NZ PL RO SG SI SK TR TT UA US UZ VN AM AZ BY KG KZ MD RU TJ TM |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): KE LS MW SD SZ UG AT BE CH DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN ML MR NE SN TD TG |
|
DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
COP | Corrected version of pamphlet |
Free format text: PAGES 11-13,CLAIMS,REPLACED BY CORRECT PAGES 11-15 |
|
ENP | Entry into the national phase |
Ref document number: 2218047 Country of ref document: CA Ref country code: CA Ref document number: 2218047 Kind code of ref document: A Format of ref document f/p: F |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1996912020 Country of ref document: EP |
|
ENP | Entry into the national phase |
Ref country code: JP Ref document number: 1996 531470 Kind code of ref document: A Format of ref document f/p: F |
|
WWE | Wipo information: entry into national phase |
Ref document number: 08945183 Country of ref document: US |
|
WWP | Wipo information: published in national office |
Ref document number: 1996912020 Country of ref document: EP |
|
WWG | Wipo information: grant in national office |
Ref document number: 1996912020 Country of ref document: EP |