US20020042439A1 - Method for controlling a population of social insects using 1-arylpyrazoles or 1-heteroarylpyrazoles - Google Patents
Method for controlling a population of social insects using 1-arylpyrazoles or 1-heteroarylpyrazoles Download PDFInfo
- Publication number
- US20020042439A1 US20020042439A1 US08/981,795 US98179598A US2002042439A1 US 20020042439 A1 US20020042439 A1 US 20020042439A1 US 98179598 A US98179598 A US 98179598A US 2002042439 A1 US2002042439 A1 US 2002042439A1
- Authority
- US
- United States
- Prior art keywords
- population
- ants
- alkyl
- composition
- radical
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 44
- 241000238631 Hexapoda Species 0.000 title claims abstract description 32
- 125000004961 1-arylpyrazolyl group Chemical group 0.000 title 1
- 241000257303 Hymenoptera Species 0.000 claims abstract description 44
- 241001674044 Blattodea Species 0.000 claims abstract description 31
- 239000000203 mixture Substances 0.000 claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 241000256856 Vespidae Species 0.000 claims abstract description 15
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 241000238659 Blatta Species 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000001188 haloalkyl group Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000000039 congener Substances 0.000 claims description 3
- 235000012907 honey Nutrition 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims description 2
- 229930091371 Fructose Natural products 0.000 claims description 2
- 239000005715 Fructose Substances 0.000 claims description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 2
- 108010064851 Plant Proteins Proteins 0.000 claims description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 2
- 229930006000 Sucrose Natural products 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- 235000021120 animal protein Nutrition 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000008121 dextrose Substances 0.000 claims description 2
- 239000003925 fat Substances 0.000 claims description 2
- 239000008103 glucose Substances 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 239000008101 lactose Substances 0.000 claims description 2
- 235000013379 molasses Nutrition 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 235000021118 plant-derived protein Nutrition 0.000 claims description 2
- 239000005720 sucrose Substances 0.000 claims description 2
- 230000006378 damage Effects 0.000 description 9
- 235000013305 food Nutrition 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 241000952627 Monomorium pharaonis Species 0.000 description 4
- 239000011149 active material Substances 0.000 description 4
- 241001124076 Aphididae Species 0.000 description 2
- 241000238657 Blattella germanica Species 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- 241000948337 Lasius niger Species 0.000 description 2
- 241001646976 Linepithema humile Species 0.000 description 2
- 241001374808 Tetramorium caespitum Species 0.000 description 2
- 0 [1*]C1=NN(C2=*C=C([13*])C=C2[11*])C([4*])=C1[2*] Chemical compound [1*]C1=NN(C2=*C=C([13*])C=C2[11*])C([4*])=C1[2*] 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 241000908424 Acromyrmex Species 0.000 description 1
- 241000726103 Atta Species 0.000 description 1
- 241000238658 Blattella Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000256602 Isoptera Species 0.000 description 1
- 241000256686 Lasius <genus> Species 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
- 241000238675 Periplaneta americana Species 0.000 description 1
- 241001510010 Periplaneta fuliginosa Species 0.000 description 1
- 241001492664 Solenopsis <angiosperm> Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000009412 basement excavation Methods 0.000 description 1
- 235000015895 biscuits Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 230000036449 good health Effects 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 244000062645 predators Species 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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
Definitions
- the subject of the present invention is a method for controlling a population of social insects, especially ants, wasps and cockroaches (or Blatta spp.) It is often very desirable to combat the drawbacks caused by populations of social insects such as ants or wasps or cockroaches (or Blatta spp.), especially in the case of ant populations.
- Social insects are insects which live in a large society, or in a colony comprising a large number of such insects or congeners.
- the control of ants is also desirable as regards the cultivation of fruit trees and/or ornamental trees.
- the reason for this is that certain species of ant provide a role of defending aphids against their predators and thus contribute towards maintaining high populations of aphids, which are harmful to the good health of the trees concerned and/or to fruit yields.
- the pharaoh ant (Monomorium pharaonis) may create anthills even inside living areas, which, in the case of blocks of flats and especially of hospitals, poses hygiene problems.
- the known methods moreover have the drawback that it is very difficult to treat all the individuals of the population, especially on account of the fact that, as regards ants, the anthills are fairly inaccessible, since they are generally located at a depth of several tens of centimeters below the surface of the ground.
- One aim of the present invention is to overcome these drawbacks.
- Another aim of the present invention is to ensure the destruction of the larvae present in the anthill, or more generally in the nest or dwelling place of the said social insects.
- Another aim of the present invention is to ensure the destruction of the laying females present in the anthill, or more generally in the nest or dwelling place of the said social insects.
- Another aim of the present invention is to propose a method which allows the definitive destruction of all or virtually all of a population of social insects such as ants or wasps or cockroaches (or Blatta spp.), preferably such as ants or cockroaches (or Blatta spp.).
- the subject of the present invention is thus a method for controlling a population of social insects such as ants or wasps or cockroaches (or Blatta spp.), characterized in that an effective amount of a composition comprising a bait and a compound of formula (I):
- R 1 is a halogen atom or a CN or methyl group
- R 2 is S(O) n R 3 ;
- R 3 is alkyl or haloalkyl
- R 4 represents a hydrogen or halogen atom; or a radical NR 5 R 6 , S(O) m R 7 , C(O)R 7 or C(O)O—R 7 , alkyl, haloalkyl or OR 8 , or a radical —N ⁇ C (R 9 ) (R 10 );
- R 5 and R 6 independently represent a hydrogen atom or an alkyl, haloalkyl, C(O) alkyl or S(O) r CF 3 radical; or R 5 and R 6 may together form a divalent alkylene radical which may be interrupted by one or two divalent hetero atoms, such as oxygen or sulphur;
- R 7 represents an alkyl or haloalkyl radical
- R 8 represents an alkyl or haloalkyl radical or a hydrogen atom
- R 9 represents an alkyl radical or a hydrogen atom
- R 10 represents a phenyl or heteroaryl group optionally substituted with one or more halogen atoms or groups such as OH, —O-alkyl, —S-alkyl, cyano or alkyl;
- R 11 and R 12 represent, independently of each other, a hydrogen or halogen atom
- R 13 represents a halogen atom or a haloalkyl, haloalkoxy, S(O) q CF 3 or SF 5 group;
- m, n, q and r represent, independently of each other, an integer equal to 0, 1 or 2;
- X represents a trivalent nitrogen atom or a radical C—R 12 , the other three valency positions of the carbon atom forming part of the aromatic ring;
- the alkyl radicals in the definition of formula (I) generally comprise from 1 to 6 carbon atoms.
- the ring formed by the divalent alkylene radical representing R 5 and R 6 , as well as by the nitrogen atom to which R 5 and R 6 are attached, is generally a 5-, 6-or 7-membered ring.
- a preferred class of compounds of formula (I) comprises the compounds where R 1 is CN and/or R 3 is haloalkyl and/or R 4 is NH 2 and/or R 11 and R 12 are, independently of one another, a halogen atom and/or R 13 is haloalkyl.
- Populations of ants are more especially preferred among the populations of social insects which may be controlled using the method according to the invention.
- control of a population of social insects such as ants, wasps or cockroaches is understood to mean the control of the said insects, and more particularly the total or virtually total destruction of the said population, in other words the destruction of more than 60%, preferably more than 70% and even more preferably of 95 to 100%, of the said population.
- An effective amount of the composition used in the method according to the invention is understood to mean an amount which is capable of controlling the whole population of social insects such as a population of ants or wasps or cockroaches (or Blatta spp.).
- the invention relates to a method for treating social insects such as ants, cockroaches or wasps with an effective amount of active material of formula (I), this effective amount of composition being an amount used equal to the dose required to destroy at least 90% of the minor fraction of the population of social insects to which the said composition is applied, within a period of between 2 and 30 days, preferably between 2 and 7 days.
- the minor fraction often corresponds in practice to the population living or circulating outside the common dwelling place or nest.
- the effective amount of composition used for the method according to the invention is generally such that the dose of compound of formula (I) is between 0.05 and 50 mg per anthill treated, preferably from 0.1 to 20 mg.
- This effective amount may be determined more precisely within this range by systematic tests, depending on the species of ant whose population it is desired to control, and also depending on the size and extent of the anthills which may vary according to the nature of these species.
- the invention thus also relates to a method for controlling social insects such as ants, wasps or cockroaches (but preferably cockroaches or Blatta spp.) which have a common dwelling place or nest in which they live with a substantial population of their congeners, the said method comprising a treatment with an effective dose, preferably a dose of between 0.0001 and 20 grams per 100 m 2 , of one or more areas frequented by, or assumed to be frequented by, the said social insects (preferably cockroaches), the said area being outside the place of the said common dwelling but being a place in which the cockroaches circulate or are assumed to circulate.
- an effective dose preferably a dose of between 0.0001 and 20 grams per 100 m 2
- the ants which may be controlled using the method according to the invention are especially:
- ants of the genus Lasius for example the black ant ( Lasius niger );
- the pavement ant Tetramorium caespitum
- fungal ants such as the ants of the genus Acromyrmex (for example the cassava ant) and the ants of the genus Atta.
- the cockroaches which may be treated by the method of the invention are mainly Blatella germanica, Blatella orientalis, Periplaneta americana, Periplaneta fuliginosa.
- the compound of formula (I) may be prepared according to one of the methods described in Patent Applications WO 87/3781, 93/6089, 94/21606, and EP 295,117 or alternatively by another method from within the general experience of those skilled in the art competent in chemical synthesis. This compound is also referred to in the remainder of the present text by the term active material.
- the bait employed in the composition used in the method according to the invention is a product which is sufficiently appetizing to incite social insects such as ants or wasps or cockroaches (or Blatta spp.) to eat it.
- this bait is chosen, for example, but not exclusively, from animal and/or plant proteins, or alternatively from fats, also of animal and/or plant origin, or even from mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose or even molasses or honey.
- the compound of formula (I) used in the invention is 5-amino-3-cyano-1-[2, 6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl) sulphinyl]-1H-pyrazole.
- the minor fraction of the population to which the composition employed in the method according to the invention is applied is generally between 1 and 50% of the total population, preferably between 2 and 20%.
- the population of ants which may be controlled using the method according to the invention is a population of ants living in the same anthill.
- the minor fraction of the population to which the composition is applied generally consists of workers whose function is to collect food from outside the anthill, these being known as the harvester workers of the anthill.
- the ant or cockroach population which can be controlled by means of the method according to the invention is a population of cockroaches living in the same common dwelling place for cockroaches.
- the dose of compound of formula (I) in the composition used is between 0.0005 and 0.5%, preferably between 0.001 and 0.2%.
- the percentages corresponding to doses are, except where otherwise mentioned, weight/weight percentages.
- the dose of bait in the composition used is generally between 1 and 99%, preferably between 30 and 99%.
- the composition used may also comprise other additives such as a solvent for the active material, a flavouring, a preserving agent, a dye or a bitter agent.
- the composition by placing it in a closed bait-carrier box containing openings which are reserved, on account of their size, for the exclusive use of ants or Blatta spp., or insects of similar size, in an area where these insects are likely to be found.
- the area may especially be in a public or private place, such as a living area, or alternatively on a balcony, a patio, in a garden or in a field.
- This variant is of improved safety, since it concerns an active material which is liable to present a risk in the case of accidental contact or ingestion by pets or children.
- compound A is 5-amino-3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulphinyl]-1H-pyrazole, referred to as compound A.
- a watch glass containing 10 g of a 0.05% dispersion of compound A in honey is placed 20 cm from the entrance to an active anthill.
- the ants are of the species Lasius niger, for which the fraction of workers whose function is to collect food is in the region of 10% of the total population.
- the total population is estimated by a count carried out on an untreated anthill, referred to as the control, containing 10,000 individuals.
- Tests are carried out on Blatella Germanica cockroaches in boxes 36 ⁇ 24 ⁇ 14 cm in size. These boxes comprise a source of water, a shelter consisting of piled pieces of cardboard, and additional food consisting of biscuit pieces.
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)
Abstract
A method for controlling a population of social insects such as ants, wasps or cockroaches by administering to a minor fraction of the population an effective amount of a composition that includes a bait and a 1-phenylpyrazole-type compound, particularly 5-amino-3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulphinyl]-1H-pyrazole.
Description
- The subject of the present invention is a method for controlling a population of social insects, especially ants, wasps and cockroaches (or Blatta spp.) It is often very desirable to combat the drawbacks caused by populations of social insects such as ants or wasps or cockroaches (or Blatta spp.), especially in the case of ant populations. Social insects are insects which live in a large society, or in a colony comprising a large number of such insects or congeners.
- In the case of ants, for example, these drawbacks generally stem from the inconvenience caused to individuals by the presence or passage of columns of ants in living areas or in the immediate vicinity thereof, such as in the garden or on the patio. The passage of such columns of ants on the lawn next to a private house may especially be particularly unpleasant for the resident wishing to relax by stretching out on the said lawn, on account of the bites inflicted by certain species.
- The control of ants is also desirable as regards the cultivation of fruit trees and/or ornamental trees. The reason for this is that certain species of ant provide a role of defending aphids against their predators and thus contribute towards maintaining high populations of aphids, which are harmful to the good health of the trees concerned and/or to fruit yields.
- Certain species of art sometimes cause even greater inconvenience. Thus, the pharaoh ant (Monomorium pharaonis) may create anthills even inside living areas, which, in the case of blocks of flats and especially of hospitals, poses hygiene problems.
- Now, the inconvenience and/or damage caused by social insects such as ants or wasps or cockroaches (or Blatta spp.), and preferably ants or cockroaches (or Blatta spp.), are in direct proportion with the sometimes very large number which a population of such insects may reach, for example, in the case of ants, the very large number of individuals in the population of an anthill.
- Methods for controlling ants or wasps or cockroaches (or Blatta spp.) using insecticidal compounds are known. However, these methods are not always satisfactory. The reason for this is that they often destroy only a small portion of the population concerned, for example, in the case of ants, a fraction of the workers whose function is to collect food outside the anthill. The destruction of this population category is not, however, sufficient to overcome the drawbacks caused by the ants. Indeed, the large capacity of ants to proliferate and their specialization based on the needs of the anthill are capable of rapidly compensating for this destruction, bringing about a new increase in the population.
- The known methods moreover have the drawback that it is very difficult to treat all the individuals of the population, especially on account of the fact that, as regards ants, the anthills are fairly inaccessible, since they are generally located at a depth of several tens of centimeters below the surface of the ground.
- One aim of the present invention is to overcome these drawbacks.
- Another aim of the present invention is to ensure the destruction of the larvae present in the anthill, or more generally in the nest or dwelling place of the said social insects.
- Another aim of the present invention is to ensure the destruction of the laying females present in the anthill, or more generally in the nest or dwelling place of the said social insects.
- Another aim of the present invention is to propose a method which allows the definitive destruction of all or virtually all of a population of social insects such as ants or wasps or cockroaches (or Blatta spp.), preferably such as ants or cockroaches (or Blatta spp.).
- It has now been found that these aims could be totally or partly achieved by means of the control method according to the invention which is described in detail below.
-
- in which:
- R 1 is a halogen atom or a CN or methyl group;
- R 2 is S(O)nR3;
- R 3 is alkyl or haloalkyl;
- R 4 represents a hydrogen or halogen atom; or a radical NR5R6, S(O)mR7, C(O)R7 or C(O)O—R7, alkyl, haloalkyl or OR8, or a radical —N═C (R9) (R10);
- R 5 and R6 independently represent a hydrogen atom or an alkyl, haloalkyl, C(O) alkyl or S(O)rCF 3 radical; or R5 and R6 may together form a divalent alkylene radical which may be interrupted by one or two divalent hetero atoms, such as oxygen or sulphur;
- R 7 represents an alkyl or haloalkyl radical;
- R 8 represents an alkyl or haloalkyl radical or a hydrogen atom;
- R 9 represents an alkyl radical or a hydrogen atom;
- R 10 represents a phenyl or heteroaryl group optionally substituted with one or more halogen atoms or groups such as OH, —O-alkyl, —S-alkyl, cyano or alkyl;
- R 11 and R12 represent, independently of each other, a hydrogen or halogen atom;
- R 13 represents a halogen atom or a haloalkyl, haloalkoxy, S(O)qCF3 or SF5 group;
- m, n, q and r represent, independently of each other, an integer equal to 0, 1 or 2;
- X represents a trivalent nitrogen atom or a radical C—R 12, the other three valency positions of the carbon atom forming part of the aromatic ring;
- with the proviso that when R 1 is methyl, then R3 is haloalkyl, R4 is NH2, R11 is Cl, R13 is CF3 and X is N.
- The alkyl radicals in the definition of formula (I) generally comprise from 1 to 6 carbon atoms. The ring formed by the divalent alkylene radical representing R 5 and R6, as well as by the nitrogen atom to which R5 and R6 are attached, is generally a 5-, 6-or 7-membered ring.
- A preferred class of compounds of formula (I) comprises the compounds where R 1 is CN and/or R3 is haloalkyl and/or R4 is NH2 and/or R11 and R12 are, independently of one another, a halogen atom and/or R13 is haloalkyl.
- Populations of ants are more especially preferred among the populations of social insects which may be controlled using the method according to the invention.
- In the sense of the present invention, control of a population of social insects such as ants, wasps or cockroaches is understood to mean the control of the said insects, and more particularly the total or virtually total destruction of the said population, in other words the destruction of more than 60%, preferably more than 70% and even more preferably of 95 to 100%, of the said population.
- An effective amount of the composition used in the method according to the invention is understood to mean an amount which is capable of controlling the whole population of social insects such as a population of ants or wasps or cockroaches (or Blatta spp.).
- More particularly, the invention relates to a method for treating social insects such as ants, cockroaches or wasps with an effective amount of active material of formula (I), this effective amount of composition being an amount used equal to the dose required to destroy at least 90% of the minor fraction of the population of social insects to which the said composition is applied, within a period of between 2 and 30 days, preferably between 2 and 7 days. The minor fraction often corresponds in practice to the population living or circulating outside the common dwelling place or nest.
- According to a more preferred variant of the invention, when the population of social insects is a population of ants, the effective amount of composition used for the method according to the invention is generally such that the dose of compound of formula (I) is between 0.05 and 50 mg per anthill treated, preferably from 0.1 to 20 mg. This effective amount may be determined more precisely within this range by systematic tests, depending on the species of ant whose population it is desired to control, and also depending on the size and extent of the anthills which may vary according to the nature of these species.
- The invention thus also relates to a method for controlling social insects such as ants, wasps or cockroaches (but preferably cockroaches or Blatta spp.) which have a common dwelling place or nest in which they live with a substantial population of their congeners, the said method comprising a treatment with an effective dose, preferably a dose of between 0.0001 and 20 grams per 100 m 2, of one or more areas frequented by, or assumed to be frequented by, the said social insects (preferably cockroaches), the said area being outside the place of the said common dwelling but being a place in which the cockroaches circulate or are assumed to circulate.
- The ants which may be controlled using the method according to the invention are especially:
- ants of the genus Lasius, for example the black ant ( Lasius niger);
- the pavement ant ( Tetramorium caespitum);
- the pharaoh ant ( Monomorium pharaonis);
- the Argentine ant ( Iridomyrmex humilis);
- fire ants belonging to the genus Solenopsis;
- fungal ants, such as the ants of the genus Acromyrmex (for example the cassava ant) and the ants of the genus Atta.
- The cockroaches which may be treated by the method of the invention are mainly Blatella germanica, Blatella orientalis, Periplaneta americana, Periplaneta fuliginosa.
- The compound of formula (I) may be prepared according to one of the methods described in Patent Applications WO 87/3781, 93/6089, 94/21606, and EP 295,117 or alternatively by another method from within the general experience of those skilled in the art competent in chemical synthesis. This compound is also referred to in the remainder of the present text by the term active material.
- The bait employed in the composition used in the method according to the invention is a product which is sufficiently appetizing to incite social insects such as ants or wasps or cockroaches (or Blatta spp.) to eat it. In the case of ants, this bait is chosen, for example, but not exclusively, from animal and/or plant proteins, or alternatively from fats, also of animal and/or plant origin, or even from mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose or even molasses or honey.
- According to a particularly advantageous variant of the invention, the compound of formula (I) used in the invention is 5-amino-3-cyano-1-[2, 6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl) sulphinyl]-1H-pyrazole.
- The minor fraction of the population to which the composition employed in the method according to the invention is applied is generally between 1 and 50% of the total population, preferably between 2 and 20%.
- According to a preferred variant of the invention, the population of ants which may be controlled using the method according to the invention is a population of ants living in the same anthill. In this case, the minor fraction of the population to which the composition is applied generally consists of workers whose function is to collect food from outside the anthill, these being known as the harvester workers of the anthill.
- According to another preferred variant of the invention, the ant or cockroach population which can be controlled by means of the method according to the invention is a population of cockroaches living in the same common dwelling place for cockroaches.
- The dose of compound of formula (I) in the composition used is between 0.0005 and 0.5%, preferably between 0.001 and 0.2%. In the present text, the percentages corresponding to doses are, except where otherwise mentioned, weight/weight percentages.
- The dose of bait in the composition used is generally between 1 and 99%, preferably between 30 and 99%. The composition used may also comprise other additives such as a solvent for the active material, a flavouring, a preserving agent, a dye or a bitter agent.
- According to a particularly advantageous variant of the method according to the invention, it is preferred to apply the composition by placing it in a closed bait-carrier box containing openings which are reserved, on account of their size, for the exclusive use of ants or Blatta spp., or insects of similar size, in an area where these insects are likely to be found. The area may especially be in a public or private place, such as a living area, or alternatively on a balcony, a patio, in a garden or in a field. This variant is of improved safety, since it concerns an active material which is liable to present a risk in the case of accidental contact or ingestion by pets or children.
- The invention as described in the present application also applies to termites, but is preferred for ants, cockroaches and wasps.
- In the examples which follow the compound of formula (I) used is 5-amino-3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulphinyl]-1H-pyrazole, referred to as compound A.
- A watch glass containing 10 g of a 0.05% dispersion of compound A in honey is placed 20 cm from the entrance to an active anthill. The ants are of the species Lasius niger, for which the fraction of workers whose function is to collect food is in the region of 10% of the total population. The total population is estimated by a count carried out on an untreated anthill, referred to as the control, containing 10,000 individuals.
- During the first 2 days, it is observed that the ants head in a column from the anthill to the watch glass, stop to take up the dispersion and then return to the anthill.
- After 15 days, no further surface activity is observed around the anthill. An update on the latter is then obtained by excavation.
- A destruction rate of greater than 99% is observed.
- In particular, all the larvae have been destroyed.
- Tests are carried out on Blatella Germanica cockroaches in boxes 36×24×14 cm in size. These boxes comprise a source of water, a shelter consisting of piled pieces of cardboard, and additional food consisting of biscuit pieces.
- 15 cockroaches are introduced into the box without bait.
- After 24 hours, a 2.7 g pellet of bait with 1.35 mg of product of formula (I) is introduced into the box.
- After a further 8 hours, the bait and the additional food are removed and 15 new healthy cockroaches are introduced.
- 64 hours after the introduction of the bait (ie. 56 hours after removing the bait and introducing new cockroaches), 98.6% of the cockroaches are dead. The level is 100% after 88 hours.
Claims (17)
1. Method for controlling a population of social insects such as ants or wasps or cockroaches (or Blatta spp.), characterized in that an effective amount of a composition comprising a bait and a compound of formula (I):
in which:
R1 is a halogen atom or a CN or methyl group;
R2 is S(O)nR3;
R3 is alkyl or haloalkyl;
R4 represents a hydrogen or halogen atom; or a radical NR5R6, S(O)mR7, C(O)R7 or C(O)O—R7, alkyl, haloalkyl or OR8 or a radical —N═C(R9)(R10);
R5 and R6 independently represent a hydrogen atom or an alkyl, haloalkyl, C(O)alkyl or S(O)rCF3 radical; or R5 and R6 may together form a divalent alkylene radical which may be interrupted by one or two divalent hetero atoms, such as oxygen or sulphur;
R7 represents an alkyl or haloalkyl radical;
R8 represents an alkyl or haloalkyl radical or a hydrogen atom;
R9 represents an alkyl radical or a hydrogen atom;
R10 represents a phenyl or heteroaryl group optionally substituted with one or more halogen atoms or groups such as OH, —O-alkyl, —S-alkyl, cyano or alkyl;
R11 and R12 represent, independently of each other, a hydrogen or halogen atom;
R13 represents a halogen atom or a haloalkyl, haloalkoxy, S(O)qCF3 or SF5 group;
m, n, q and r represent, independently of each other, an integer equal to 0, 1 or 2;
X represents a trivalent nitrogen atom or a radical C—R12, the other three valency positions of the carbon atom forming part of the aromatic ring;
with the proviso that when R1 is methyl, then R3 is haloalkyl, R4 is NH2, R11 is Cl, R13 is CF3 and X is N.
2. Method according to claim 1 , characterized in that the controlled population of social insects is a population of ants.
3. Method according to claim 1 , characterized in that the controlled population of social insects is a population of cockroaches.
4. Method for controlling social insects such as ants, wasps or cockroaches (but preferably cockroaches or Blatta spp.) which have a common dwelling place or nest in which they live with a substantial population of their congeners, the said method comprising a treatment with an effective dose, preferably a dose of between 0.0001 and 20 grams per 100 m2, of one or more areas frequented by, or assumed to be frequented by, the said social insects, the said area being outside the place of the said common dwelling but being a place in which the cockroaches circulate or are assumed to circulate.
5. Method according to one of the preceding claims, characterized in that the effective amount of composition used is an amount which is capable of controlling the whole population of social insects.
6. Method according to one of the preceding claims, characterized in that the effective amount of composition used is equal to the dose required to destroy at least 90% of the minor fraction of the population of social insects to which said composition is applied, in a time between 2 and 30 days, preferably between 2 and 7 days.
7. Method according to one of the preceding claims, characterized in that the effective amount of composition used for the method according to the invention is such that the dose of compound of formula (I) is between 0.05 and 50 mg per anthill treated, preferably from 0.1 to 20 mg.
8. Method according to one of the preceding claims, characterized in that the effective amount of composition used for the method according to the invention is such that the dose of compound of formula (I) is between 0.0001 and 20 g per 100 m2.
9. Method according to one of the preceding claims, characterized in that the bait employed is chosen from animal and/or plant proteins, or alternatively from fats, also of animal and/or plant origin, or even from mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose or even molasses or honey.
10. Method according to one of the preceding claims, characterized in that the compound of formula (I) used is 5-amino-3-cyano-1-[2,6-dichloro-4-(trifluoro-methyl)phenyl]-4-[(trifluoromethyl)sulphinyl]-1H-pyrazole.
11. Method according to one of the preceding claims, characterized in that the composition is applied to a fraction of the population which is between 1 and 40% of the total population, preferably between 2 and 20%.
12. Method according to one of the preceding claims, characterized in that the controlled population of ants is a population of ants living in the same anthill.
13. Method according to claim 10 , characterized in that the minor fraction of the population to which the composition is applied consists of harvester workers from the anthill.
14. Method according to one of the preceding claims, characterized in that the dose of compound of formula (I) in the composition is between 0.0005 and 0.5%, preferably between 0.001 and 0.2%.
15. Method according to one of the preceding claims, characterized in that the dose of bait in the composition is between 1 and 99%, preferably between 30 and 99%.
16. Method according to one of the preceding claims, characterized in that the composition is applied by placing it in a closed bait carrier box containing openings which are reserved, on account of their size, for the exclusive use of ants or Blatta spp., in an area where these are likely to be found.
17. Method according to claim 16 , characterized in that the area is in a public or private place, such as a living area, or alternatively on a balcony, a patio, in a garden or in a field.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/386,908 US7138422B2 (en) | 1995-06-29 | 2003-03-12 | Method for controlling a population of social insects using 1-arylpyrazoles or 1-heteroarylpyrazoles |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR95/08074 | 1995-06-29 | ||
| FR9508074A FR2735951A1 (en) | 1995-06-29 | 1995-06-29 | Control of social insects such as ants and cockroaches |
| FR96/01238 | 1996-01-29 | ||
| FR9601238A FR2735952B1 (en) | 1995-06-29 | 1996-01-29 | METHOD FOR CONTROLLING A POPULATION OF SOCIAL INSECTS |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/FR1996/000994 A-371-Of-International WO1997001279A1 (en) | 1995-06-29 | 1996-06-26 | Method for controlling a population of social insects using 1-arylpyrazoles or 1-heteroarylpyrazoles |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US10/386,908 Continuation US7138422B2 (en) | 1995-06-29 | 2003-03-12 | Method for controlling a population of social insects using 1-arylpyrazoles or 1-heteroarylpyrazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20020042439A1 true US20020042439A1 (en) | 2002-04-11 |
Family
ID=26232075
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US08/981,795 Abandoned US20020042439A1 (en) | 1995-06-29 | 1996-06-26 | Method for controlling a population of social insects using 1-arylpyrazoles or 1-heteroarylpyrazoles |
| US10/386,908 Expired - Fee Related US7138422B2 (en) | 1995-06-29 | 2003-03-12 | Method for controlling a population of social insects using 1-arylpyrazoles or 1-heteroarylpyrazoles |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US10/386,908 Expired - Fee Related US7138422B2 (en) | 1995-06-29 | 2003-03-12 | Method for controlling a population of social insects using 1-arylpyrazoles or 1-heteroarylpyrazoles |
Country Status (23)
| Country | Link |
|---|---|
| US (2) | US20020042439A1 (en) |
| EP (1) | EP0836387B1 (en) |
| JP (1) | JPH11508551A (en) |
| KR (1) | KR100428232B1 (en) |
| CN (2) | CN1102832C (en) |
| AP (1) | AP951A (en) |
| AR (1) | AR002646A1 (en) |
| AT (1) | ATE322824T1 (en) |
| AU (1) | AU710851B2 (en) |
| BR (1) | BR9609465A (en) |
| CA (1) | CA2223822C (en) |
| CO (1) | CO4750583A1 (en) |
| DE (1) | DE69636034T2 (en) |
| DK (1) | DK0836387T3 (en) |
| EA (1) | EA002017B1 (en) |
| ES (1) | ES2257750T3 (en) |
| FR (1) | FR2735952B1 (en) |
| MX (1) | MX9800139A (en) |
| MY (1) | MY114788A (en) |
| NZ (1) | NZ312722A (en) |
| PT (1) | PT836387E (en) |
| TW (1) | TW349842B (en) |
| WO (1) | WO1997001279A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080152617A1 (en) * | 2004-05-10 | 2008-06-26 | Fmc Corporation | Composition for Control of Cockroaches |
| US20110236451A1 (en) * | 2008-11-25 | 2011-09-29 | Basf Se | Multipurpose Ant Bait |
| US20180139960A1 (en) * | 2015-04-17 | 2018-05-24 | Basf Agrochemical Products B.V. | Method for controlling non-crop pests |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0987111A (en) * | 1995-09-27 | 1997-03-31 | Sumitomo Chem Co Ltd | Poison bait for pest control |
| AU1031199A (en) * | 1997-10-07 | 1999-04-27 | Rhone-Poulenc Agro | Methode of insect control |
| BR9705278A (en) * | 1997-10-15 | 1999-05-25 | Rhone Poulenc Agrochimie | Composition method to control cut leaf ants and commercial product |
| CN1204123C (en) * | 2002-07-30 | 2005-06-01 | 王正权 | N-phenyl pyrazole derivative pesticide |
| WO2021039758A1 (en) * | 2019-08-27 | 2021-03-04 | アース製薬株式会社 | Poison bait for bees |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5232940A (en) * | 1985-12-20 | 1993-08-03 | Hatton Leslie R | Derivatives of N-phenylpyrazoles |
| US5306694A (en) * | 1991-01-18 | 1994-04-26 | Rhone-Poulenc Inc. | Pesticidal 1-(2-pyridyl)-pyrazole |
| US5451598A (en) * | 1991-09-27 | 1995-09-19 | Zeneca Limited | Heterocyclic compounds and insecticidal use |
| US5516787A (en) * | 1993-12-20 | 1996-05-14 | Sumitomo Chemical Company, Limited | Insecticidal/acaricidal composition |
| US5547974A (en) * | 1985-12-20 | 1996-08-20 | Rhone-Poulenc Agriculture Ltd. | Derivatives of N-phenylpyrazoles |
| US5567429A (en) * | 1993-12-21 | 1996-10-22 | Sumitomo Chemical Company, Limited | Pest controlling composition |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3200909A1 (en) * | 1982-01-14 | 1983-07-21 | Bayer Ag, 5090 Leverkusen | "ANTI-COAT, METHOD FOR THE PRODUCTION AND USE THEREOF" |
| JPH0617290B2 (en) * | 1985-10-29 | 1994-03-09 | アース製薬株式会社 | Ant attractant composition |
| GB8713768D0 (en) * | 1987-06-12 | 1987-07-15 | May & Baker Ltd | Compositions of matter |
| GB8531485D0 (en) * | 1985-12-20 | 1986-02-05 | May & Baker Ltd | Compositions of matter |
| GB9306184D0 (en) * | 1993-03-25 | 1993-05-19 | Zeneca Ltd | Heteroaromatic compounds |
| IL116148A (en) * | 1994-11-30 | 2001-03-19 | Rhone Poulenc Agrochimie | Emulsifiable composition for the control of insects |
| IL116147A (en) * | 1994-11-30 | 2002-05-23 | Aventis Cropscience Sa | Emulsifiable composition for the control of insects |
| CA2209824C (en) * | 1995-01-09 | 2000-05-09 | Heidi J. Uick | Liquid insect bait |
| US5614182A (en) * | 1995-04-10 | 1997-03-25 | Rhone-Poulenc Inc. | Methods of attracting and combatting insects |
| FR2735950B1 (en) * | 1995-06-29 | 1997-08-01 | Rhone Poulenc Agrochimie | INSECTICIDE COMPOSITIONS BASED ON A PHENYLPYRAZOLE DERIVATIVE, IN PARTICULAR FOR FIGHTING ANTS |
| JPH0987111A (en) * | 1995-09-27 | 1997-03-31 | Sumitomo Chem Co Ltd | Poison bait for pest control |
-
1996
- 1996-01-29 FR FR9601238A patent/FR2735952B1/en not_active Expired - Lifetime
- 1996-06-26 PT PT96924022T patent/PT836387E/en unknown
- 1996-06-26 AT AT96924022T patent/ATE322824T1/en active
- 1996-06-26 EP EP96924022A patent/EP0836387B1/en not_active Expired - Lifetime
- 1996-06-26 AP APAP/P/1998/001186A patent/AP951A/en active
- 1996-06-26 BR BR9609465A patent/BR9609465A/en not_active Application Discontinuation
- 1996-06-26 WO PCT/FR1996/000994 patent/WO1997001279A1/en not_active Ceased
- 1996-06-26 KR KR1019970709839A patent/KR100428232B1/en not_active Expired - Lifetime
- 1996-06-26 CA CA002223822A patent/CA2223822C/en not_active Expired - Lifetime
- 1996-06-26 CN CN96196221A patent/CN1102832C/en not_active Expired - Lifetime
- 1996-06-26 EA EA199800100A patent/EA002017B1/en not_active IP Right Cessation
- 1996-06-26 JP JP9504205A patent/JPH11508551A/en active Pending
- 1996-06-26 ES ES96924022T patent/ES2257750T3/en not_active Expired - Lifetime
- 1996-06-26 AU AU64618/96A patent/AU710851B2/en not_active Expired
- 1996-06-26 DE DE69636034T patent/DE69636034T2/en not_active Expired - Lifetime
- 1996-06-26 DK DK96924022T patent/DK0836387T3/en active
- 1996-06-26 US US08/981,795 patent/US20020042439A1/en not_active Abandoned
- 1996-06-26 NZ NZ312722A patent/NZ312722A/en not_active IP Right Cessation
- 1996-06-27 TW TW085107779A patent/TW349842B/en active
- 1996-06-28 MY MYPI96002669A patent/MY114788A/en unknown
- 1996-06-28 AR ARP960103384A patent/AR002646A1/en active IP Right Grant
- 1996-07-02 CO CO96034470A patent/CO4750583A1/en unknown
-
1998
- 1998-01-07 MX MX9800139A patent/MX9800139A/en active IP Right Grant
-
2002
- 2002-02-25 CN CNB021053596A patent/CN1204810C/en not_active Expired - Lifetime
-
2003
- 2003-03-12 US US10/386,908 patent/US7138422B2/en not_active Expired - Fee Related
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5232940A (en) * | 1985-12-20 | 1993-08-03 | Hatton Leslie R | Derivatives of N-phenylpyrazoles |
| US5547974A (en) * | 1985-12-20 | 1996-08-20 | Rhone-Poulenc Agriculture Ltd. | Derivatives of N-phenylpyrazoles |
| US5306694A (en) * | 1991-01-18 | 1994-04-26 | Rhone-Poulenc Inc. | Pesticidal 1-(2-pyridyl)-pyrazole |
| US5451598A (en) * | 1991-09-27 | 1995-09-19 | Zeneca Limited | Heterocyclic compounds and insecticidal use |
| US5516787A (en) * | 1993-12-20 | 1996-05-14 | Sumitomo Chemical Company, Limited | Insecticidal/acaricidal composition |
| US5567429A (en) * | 1993-12-21 | 1996-10-22 | Sumitomo Chemical Company, Limited | Pest controlling composition |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080152617A1 (en) * | 2004-05-10 | 2008-06-26 | Fmc Corporation | Composition for Control of Cockroaches |
| US20110236451A1 (en) * | 2008-11-25 | 2011-09-29 | Basf Se | Multipurpose Ant Bait |
| US8840909B2 (en) | 2008-11-25 | 2014-09-23 | Basf Se | Multipurpose ant bait |
| US20180139960A1 (en) * | 2015-04-17 | 2018-05-24 | Basf Agrochemical Products B.V. | Method for controlling non-crop pests |
| US11234436B2 (en) * | 2015-04-17 | 2022-02-01 | Basf Agrochemical Products B.V. | Method for controlling non-crop pests |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3986085B2 (en) | Novel 5-amino-3-cyano-4-ethylsulfinyl-1-phenyl-pyrazole compounds and their use as agricultural chemicals | |
| EA003186B1 (en) | Pesticidal 1-arylpyrazoles | |
| FI120396B (en) | Pesticidal 1-aryl-5- (substituted alkylidenimino) pyrazoles | |
| RU2077201C1 (en) | Derivatives of 1-phenylimidazole, method of struggle against agriculture pests and composition for pesticide treatment | |
| US7138422B2 (en) | Method for controlling a population of social insects using 1-arylpyrazoles or 1-heteroarylpyrazoles | |
| KR100602814B1 (en) | Insecticidal 1-arylpyrazole | |
| Stevens et al. | Attractiveness of bait matrices and matrix/toxicant combinations to the citrus pests Iridomyrmex purpureus (F. Smith) and Iridomyrmex rufoniger gp sp.(Hym., Formicidae) | |
| EP0828420B1 (en) | A method for controlling flies infesting mushrooms by using a n-arylpyrazole or a n-heteroarylpyrazole compound | |
| HK1056098B (en) | Method for controlling a population of social insects using 1-arylpyrazoles or 1-heteroarylpyrazoles | |
| FR2735951A1 (en) | Control of social insects such as ants and cockroaches |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: RHONE-POULENC JARDIN, FRANCE Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:ZANGIACOMI, LOUIS;REEL/FRAME:009394/0486 Effective date: 19980124 |
|
| STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |
|
| AS | Assignment |
Owner name: BASF AGRO B.V. ARNHEM (NL) - WADENSWIL BRANCH, SWI Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:JARDIN, RHONE-POULENC;REEL/FRAME:015140/0993 Effective date: 20030910 |