TREA

Ectoparasitic insect pest controllers for animals and their usage

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Information

  • Patent Grant
  • 6903237
  • Patent Number
    6,903,237
  • Date Filed
    Tuesday, October 16, 2001
    23 years ago
  • Date Issued
    Tuesday, June 7, 2005
    19 years ago
Information
Abstract
Ectoparasitic insect pest controllers for animals, containing hydrazine derivatives of the general formula (I) as the active ingredient, and methods for application of the same: (I) [wherein A is (II), (III), (IV), (V) (wherein R4 and R5 are each H, C1-6 alkyl, or the like; and X is H, or one to five substituents selected from among halogeno and optionally halogenated C1-6 alkyl groups); R1 is H or C1-6 alkyl; R2 and R3 are each H, OH, C1-6 alkyl, phenylcarbonyl, or the like; Y is H, or one to five substituents selected from among halogeno, nitro, and cyano; Z is halogeno, cyano, C1-6 alkyl, or the like; and W is O or S]. The insect pest controllers exert remarkable controlling effects on parasitic insect pests harmful to domestic or pet animals, e.g. fleas, lice, ticks.
Description
TECHNICAL FIELD

This invention relates to novel ectoparasitic insect pest controllers for animals containing a hydrazine derivative as the active ingredient, and method for application of the same.


BACKGROUND ART

The hydrazine derivatives represented by the general formula (I) which are used as an active ingredient of the ectoparasitic insect pest controllers for animals of this invention are known compounds disclosed in JP-A-5-4958, JP-A-5-17428, JP-A-5-32603 and JP-A-5-262712, wherein is mentioned that these compounds, as an agrihorticultural insecticide, have a controlling effect on Lepidopterous insect pests such as diamondback moth (Plutella xylostella (Linnaeus)), rice leafroller (Cnaphalocrosis medinalis (Guenee)), etc.; Hemipterous insect pests such as tea green leafhopper (Empoasca onukii Matsuda), pear lace bug (Stephanitis nashi Esaki et Takeya), etc.; Coleopterous insect pests such as twenty-eight-spotted ladybird (Epilachna vigintioctopunctata (Fabricius)), maize weevil (Sitophilus zeamais Motschulsky), etc.; Dipterous insect pests such as melon fly (Dacus (Zeugodacus) cucurbitae Coquillett), muscid flies (Muscidae), Culex pipiens molestus, etc.; and tylenchid insect pests such as coffee root lesion nematode (Pratylenchus coffeae (Zimmermann) Filipjev et Schuurmans Stekhoven), root-knot nematode (Meloidogyne sp.), etc. However, in the above-mentioned prior arts, neither mention nor suggestion is made as to the insecticidal effect of these compounds on the ectoparasitic insect pests of animals such as insect pests belonging to fleas, lice and ticks.


A variety of chemicals have so far been proposed as an agent for controlling the ectoparasitic insect pests harmful to bred animals such as domestic and pet animals. However, an agent capable of exhibiting a high controlling effect on the ectoparasitic insect pests at a low dose is not yet known, and creation of such a novel agent is waited for.


The present inventors have conducted extensive studies with the aim of creating a novel agent exerting a remarkable controlling effect on the ectoparasitic insect pests of domestic and pet animals at a low dose. As a result, it has been found that some of the compounds selected from the hydrazine derivatives described in the above-mentioned prior arts have a remarkable controlling effect on the ectoparasitic insect pests of animals. Based on this finding, this invention has been accomplished.


DISCLOSURE OF THE INVENTION

This invention relates to an ectoparasitic insect pest controller for animals which contains, as active ingredient thereof, a hydrazine derivative represented by the following general formula (I):
embedded image

wherein A represents
embedded image

(in this formula, R4 represents a hydrogen atom or a C1-6alkyl group; X which may be the same or different represents one to five substituents selected from the group consisting of hydrogen atom, halogen atom, C1-6alkyl group and halo C1-6alkyl group);
embedded image

(in this formula, R4 and X are as defined above, and R5 represents a hydrogen atom, a C1-6alkylcarbonyl group or a phenylcarbonyl group which may optionally have one or two, the same or different substituents selected from C1-6alkyl groups);
embedded image

(in this formula, R4 and X are as defined above), or
embedded image

(in this formula, R4 and X are as defined above);

    • R1 represents a hydrogen atom or a C1-6alkyl group;
    • R2 and R3 which may be the same or different, each represents a hydrogen atom, a hydroxyl group, a C1-6alkyl group, a C1-6alkoxy group, a C1-6alkylcarbonyl group or a phenylcarbonyl group;
    • Y which may be the same or different, represents one to five substituents selected from the group consisting of hydrogen atom, halogen atom, nitro group and cyano group;
    • Z represents a halogen atom, a cyano group, a C1-6alkyl group, a halo C1-6alkyl group, a C1-6alkoxy group, a halo C1-6alkoxy group, a halo C1-6alkylthio group, a halo C1-6alkylsulfinyl group or a halo C1-6alkylsulfonyl group; and
    • W represents an oxygen atom or a sulfur atom; and to a method for using said insect pest controller.


The ectoparasitic insect pest controller for animals of this invention exerts a remarkable controlling effect on the parasitic insect pests harmful to domestic and pet animals, such as fleas, lice, ticks, etc.







BEST MODE FOR CARRYING OUT THE INVENTION

In the definition of the general formula (I) of this invention, “halogen atom” means chlorine atom, bromine atom, iodine atom or fluorine atom; “C1-6alkyl” means a straight or branched chain alkyl group having 1-6 carbon atoms; and “halo C1-6alkyl” means an alkyl group having 1-6 carbon atoms, substituted with at least one halogen atoms which may be the same or different. The hydrazine derivatives represented by the general formula (I) used as an active ingredient of the ectoparasitic insect pesst controller for animals of this invention can be produced according to the production processes mentioned in JP-A-5-4958, JP-A-5-17428, JP-A-5-32603 and JP-A-5-262712.


Among the hydrazine derivatives of this invention represented by the general formula (I), preferable are the hydrazine derivatives represented by the general formulas (I-1) and (I-2) and, in such preferable compounds, the substituent W is an oxygen atom, the substituent X is a trifluoromethyl group, the substituent Y is a cyano group, the substituent Z is a trifluoromethoxy group, and R1, R2, R3 and R4 simultaneously represent a hydrogen atom. As a further preferable compound, for example, (E)-2-[2-(4-cyanophenyl)-1-(3-trifluoromethylphenyl)ethylidene]-N-(4-trifluoromethoxyphenyl)hydrazine carboxamide can be referred to.


Next, typical examples of the hydrazine derivative represented by the general formula (I) which is an active ingredient of the ectoparasitic insect pest controller for animals of this invention will be shown in the following Tables 1 to 4. This invention, however, is not limited by these compounds. In the tables, Ph means a phenyl group.









TABLE 1







General formula (I-1)







(I-1)









embedded image


















No
R1
R2
R3
R4
X
Y
Z
W
mp° C.





 1
H
H
H
H
H
H
Cl
O
199


 2
H
H
H
H
H
H
OCF3
O
149


 3
H
H
H
H
H
4-Cl
Cl
O
206


 4
H
H
H
H
H
4-Cl
OCF3
O
197


 5
H
H
H
H
H
4-CN
Cl
O
217


 6
H
H
H
H
H
4-CN
Cl
S
128


 7
H
H
H
H
H
4-CN
OCF3
S
116


 8
H
H
H
H
H
4-CN
OCF3
O
214











E-form


 9
H
H
H
H
H
4-CN
OCF3
O
159











Z-form


10
H
H
H
H
H
4-NO2
Cl
O
222


11
H
H
H
H
H
4-NO2
Cl
S
206


12
H
H
H
H
H
4-NO2
OCF3
O
189


13
H
H
H
H
H
4-NO2
OCF3
S
139


14
H
H
H
H
H
4-NO2
SCF3
O
200


15
H
H
H
H
3-Cl
H
OCF3
O
212


16
H
H
H
H
3-Cl
4-Cl
OCF3
O
201


17
H
H
H
H
3-Cl
4-CN
Cl
O
206


18
H
H
H
H
3-Cl
4-CN
OCF3
O
187











E-form


19
H
H
H
H
3-Cl
4-CN
OCF3
O
148











Z-form


20
H
H
H
H
3-Cl
4-CN
OCF3
S
199


21
H
H
H
H
3-Cl
4-CN
SCF3
O
215


22
H
H
H
H
3-Cl
4-CN
SOCF3
O
205


23
H
H
H
H
3-Cl
4-CN
SO2CF3
O
212


24
H
H
H
H
3-Br
H
Cl
O
191


25
H
H
H
H
3-Br
H
OCF3
O
209


26
H
H
H
H
3-Br
4-CN
Cl
O
205


27
H
H
H
H
3-Br
4-CN
OCF3
O
176


28
H
H
H
H
3-Br
4-CN
SCF3
O
206


29
H
H
H
H
3-Br
4-CN
SOCF3
O
216


30
H
H
H
H
3-Br
4-CN
SO2CF3
O
215


31
H
H
H
H
3-F
H
Cl
O
206


32
H
H
H
H
3-F
H
OCF3
O
200


33
H
H
H
H
3-F
4-Cl
OCF3
O
191


34
H
H
H
H
3-F
4-Cl
Cl
O
208


35
H
H
H
H
3-F
4-CN
OCF3
O
202


36
H
H
H
H
3-I
4-CN
Cl
O
213


37
H
H
H
H
3-I
4-CN
OCF3
O
201


38
H
H
H
H
3-CH3
H
Cl
O
185


39
H
H
H
H
3-CH3
H
OCF3
O
198


40
H
H
H
H
3-CH3
4-CN
Cl
O
200


41
H
H
H
H
3-CH3
4-CN
OCF3
O
189


42
H
H
H
H
3-CF3
H
Cl
O
206


43
H
H
H
H
3-CF3
H
OCF3
O
210


44
H
H
H
H
3-CF3
4-CN
OCF3
O
191


45
H
H
H
H
3-CF3
4-CN
OCF3
S
149


46
CH3
H
H
H
H
H
Cl
O
132


47
CH3
H
H
H
H
H
OCF3
O
108


48
H
CH3
H
H
H
H
Cl
O
98


49
H
CH3
H
H
H
H
Br
O
85


50
H
CH3
H
H
H
H
OCF3
O
115











EZ-form


51
H
CH3
H
H
H
H
OCF3
O
95











E-form


52
H
CH3
H
H
H
H
OCF3
O
66











Z-form


53
H
CH3
H
H
H
4-Cl
Cl
O
121


54
H
CH3
H
H
H
4-Cl
OCF3
O
105


55
H
CH3
H
H
3-Cl
4-CN
Cl
O
140


56
H
CH3
H
H
3-Cl
4-CN
OCF3
O
98


57
H
H
OH
H
H
H
Cl
O
188


58
H
H
OH
H
H
H
OCF3
O
170


59
H
H
OH
H
H
4-Cl
Cl
O
Viscous











material


60
H
H
OH
H
H
4-Cl
OCF3
O
185











E-form


61
H
H
OH
H
H
4-Cl
OCF3
O
95











Z-form


62
H
H
OH
H
H
4-CN
Cl
O
Viscous











material


63
H
H
OH
H
H
4-CN
OCF3
O
113


64
H
H
CH3
H
H
H
Cl
O
164


65
H
H
CH3
H
H
H
OCF3
S
118


66
H
H
OCH3
H
H
H
Cl
O
183


67
H
H
OCH3
H
H
H
OCF3
O
181


68
H
H
OC3H7-i
H
H
H
Cl
O
155


69
H
H
OC3H7-i
H
H
H
OCF3
O
193


70
H
H
OC4H9-i
H
H
H
Cl
O
176


71
H
H
OC4H9-i
H
H
H
OCF3
O
184


72
H
H
O—CO—CH3
H
H
H
OCF3
O
182


73
H
H
O—CO—Ph
H
H
H
OCF3
O
168


74
H
H
OH
CH3
H
H
Cl
O
115


75
H
H
OH
CH3
H
H
OCF3
O
130


76
H
H
H
H
3-F
4-CN
SCF3
O
214


77
H
H
H
H
3-F
4-CN
SOCF3
O
214


78
H
H
H
H
4-F
4-CN
SO2CF3
O
165


79
H
H
H
H
3-Cl
4-CN
SOCF3
O
157


80
H
H
H
H
3-CF3
4-CN
SCF3
O
215


81
H
H
H
H
3-CF3
4-CN
SOCF3
O
210


82
H
H
H
H
3-CF3
4-CN
OCF3
O
152











Z-form


83
H
H
H
H
3-CF3
4-CN
Cl
O
165
















TABLE 2







General Formula (I-2)







(I-2)









embedded image




(R1 and R3 are hydrogen atoms.)















No
R2
R4
R5
X
Y
Z
W
mp° C.


















84
H
H
H
H
H
Cl
O
211


85
H
H
H
H
H
OCF3
O
194


86
H
H
H
H
4-Cl
OCF3
O
209


87
H
H
H
H
4-CN
OCF3
O
204


88
H
H
H
H
4-NO2
OCF3
O
203


89
H
H
H
3-F
4-Cl
OCF3
O
203


90
H
H
H
3-Cl
4-Cl
OCF3
O
176


91
H
H
H
3-Cl
4-CN
OCF3
O
193


92
H
H
H
3-Cl
4-CN
SCF3
O
177


93
H
H
H
3-Cl
4-CN
SOCF3
O
178


94
H
H
H
3-Cl
4-CN
SO2CF3
O
170


95
H
H
H
3-Br
4-CN
OCF3
O
187


96
H
H
H
3-CF3
4-CN
OCF3
O
165


97
H
H
H
3-CF3
4-CN
SCF3
O
164


98
H
H
H
H
4-Cl
OCF3
S
171


99
H
H
H
3-Cl
4-CN
OCF3
S
149


100
H
H
H
3-CF3
4-CN
OCF3
S
209


101
H
H
CO—CH3
3-Cl
4-CN
OCF3
O
178


102
H
H
CO—Ph
3-Cl
4-CN
OCF3
O
221


103
H
H
CONHC2H5
3-Cl
4-CN
OCF3
O
201


104
H
OH
H
H
H
OCF3
O
190


105
H
OCH3
H
H
H
Cl
O
195


106
H
OCH3
H
H
H
OCF3
O
183


107
H
OCH3
H
H
H
OCF3
O
186


108
CH3
H
H
3-Cl
4-CN
OCF3
O
156


109
H
H
H
H
4-F
OCF3
O
209


110
H
H
H
H
4-Br
Cl
O
233


111
H
H
H
H
4-Br
OCF3
O
201


112
H
H
H
H
3-CN
OCF3
O
176


113
H
H
H
H
2-NO2
OCF3
O
197


114
H
H
H
3-F
4-CN
OCF3
O
189


115
H
H
H
3-F
4-CN
SCF3
O
189


116
H
H
H
3-F
4-CN
SOCF3
O
166


117
H
H
H
3-CF3
4-CN
OCF3
O
131










−Isomer


118
H
H
H
3-CF3
4-CN
OCF3
O
126










+Isomer


119
H
H
H
3-CF3
4-CN
SOCF3
O
Glassy










material


120
H
H
H
3-CF3
4-CN
SO2CF3
O
Glassy










material


121
H
H
H
H
3-CN
OCF3
O
120





Notes: In this table, Ph represents a phenyl group. Compound Nos. 106 and 107 are diastereomers. Compound No. 106 is higher than Compound No. 107 in Rf value.













TABLE 3







General formula (I-3)







(I-3)









embedded image




(In this table, R2 and R3 are hydrogen atoms,


and W is an oxygen atom.)



















mp° C.


No
R1
R4
X
Y
X
Refractive index





122
H
H
H
H
OCF3
113.3-114.0


123
H
H
H
4-Cl
OCF3
137.8


124
H
H
H
4-CN
Cl
163


125
H
H
H
4-CN
OCF3
138


126
H
H
3-Cl
4-Cl
Cl
143.5-144.0


127
H
H
3-Cl
4-Cl
OCF3
139.6-141.5


128
H
H
3-Cl
4-NO2
Cl
174.0-176.5


129
H
H
3-Cl
4-NO2
OCF3
151.6-151.7


130
H
H
3-Cl
4-CN
Cl
191.0-192.0


131
H
H
3-Cl
4-CN
OCF3
160.5-162.0


132
H
H
3-Cl
4-CN
SCF3
188.0


133
H
H
3-Cl
4-CN
SOCF3
206.1


134
H
H
3-F
4-CN
Cl
154-156


135
H
H
3-F
4-CN
OCF3
155.9-156.8


136
H
H
3-CH3
4-CN
Cl
127


137
H
H
3-CH3
4-CN
OCF3
166


138
H
H
3-CF3
4-CN
Cl
164-165


139
H
H
3-CF3
4-CN
OCF3
151.0


140
H
CH3
3-Cl
4-CN
OCF3
nD 1.5950(25° C.)


141
CH3
H
3-CF3
4-CN
Cl
209-211


142
H
H
3-Cl
2-CN
OCF3
148
















TABLE 4







General formula (I-4)







(I-4)









embedded image




(In this formula, R1, R2, R3 and R4 are hydrogen


atoms, and W is an oxygen atom.)















mp° C.


No
X
Y
Z
Refractive index





143
H
H
OCF3
51.0-53.0


144
H
4-Cl
OCF3
92.1


145
H
4-CN
Cl
106-108


146
H
4-CN
OCF3
nD 1.5685 (27° C.)


147
3-Cl
4-Cl
Cl
105.3-106.4


148
3-Cl
4-Cl
OCF3
38.0


149
3-Cl
4-NO2
Cl
Viscous material


150
3-Cl
4-NO2
OCF3
Viscous material


151
3-Cl
4-CN
Cl
153.1


152
3-Cl
4-CN
OCF3
43.5-45.0


153
3-F
4-CN
Cl
164-165


154
3-F
4-CN
OCF3
nD 1.5615 (27° C.)


155
3-CH3
4-CN
Cl
138-139


156
3-CH3
4-CN
OCF3
nD 1.5315 (28° C.)


157
3-CF3
4-CN
Cl
43


158
3-CF3
4-CN
OCF3
153.1









Some of the compounds shown in Tables 1 to 4 are viscous substances or glassy substances. 1H-NMR date of these compounds are shown in Table 5.













No

1H-NMR [CDCl3/TMS, δ value (ppm)]
















59
6.29(s, 1H), 7.65-7.92(m, 13H), 9.14(bs, 1H),



10.70(bs, 1H). (DMSO-d6)


62
3.88(bs, 1H), 3.87(s, 1H), 6.91-7.55(m, 13H),



7.73(s, 1H), 8.13(bs, 1H).


119
3.12(dd, 1H), 3.23(dd, 1H), 4.12-4.32(m, 2H),



6.13(bs, 1H), 7.24-7.93(m, 12H), 8.08(bs, 1H).


120
3.11(dd, 1H), 3.23(dd, 1H), 4.13-4.28(m, 2H),



5.97(s, 1H), 7.25-7.75(m, 12H), 7.90-8.00(bs, 1H).


149
3.65(d, 2H), 4.20(t, 1H), 4.70(s, 2H),



6.85(dd, 1H), 6.93(dd, 1H), 7.08(dd, 1H), 7.15-



7.21 (m, 3H), 7.24(d, 2H), 7.40(d, 2H), 8.13(d, 2H),



8.40 (s, 1H).


150
3.64(s, 2H), 4.69(s, 2H), 6.84(dd, 1H),



6.94 (dd, 1H), 7.09(m, 3H), 7.23(t, 1H),



7.29(d, 2H), 7.40(d, 2H), 8.12(d, 2H), 8.40(s, 1H).









The ectoparasitic insect pest controller for animals of this invention can be used for domestic animals such as cattle, horse, sheep, etc.; and pets such as dog, cat, etc.; as well as for Rodential animals such as mouse, rat, hamster, squirrel, etc.; Lagomorphous animals, Carnivorous animals such as ferret, etc.; and birds such as duck, chicken, pigeon, etc. As the ectoparasitic pest insects of these animals, for example, the insects belonging to fleas such as















cat flea
(Ctenocephalides felis),


dog flea
(Ctenocephalides canis),


oriental rat flea
(Xenopsylla cheopis), etc.; the



insects belonging to ticks such as


Haemaphysalis longicornis,
(Boophilus microplus), etc.; and


cattle tick
the insects belonging to lice such as


cattle louse
(Haematopinus eurysternus),


sheep louse
(Damalinia ovis), etc. can be



referred to.









For an effective use of the ectoparasitic insect pest controllers for animals of this invention represented by the general formula (1), the controller is compounded with an appropriate solid carrier and/or liquid carrier and, if necessary, adjuvants and the like in an appropriate proportion according to the conventional recipe in the drug making and fixed on the carriers by dissolution, suspension, mixing, impregnation, adsorption or adhesion. The resulting mixture is formed into an appropriate preparation form such as liquid preparation, emulsion, cream, ointment, suspension, aerosol, etc. according to the purpose of the use, and then the formed preparation is put to use.


The solid or liquid carriers used in this invention may be the carriers conventionally used for agents for animals. From the viewpoint of easiness of treatment on the objective animals, the use of liquid carriers is preferable. As examples of the liquid carrier, alcohols such as methyl alcohol, ethyl alcohol, isopropyl alcohol, tertiary butyl alcohol, benzyl alcohol and the like; propylene carbonate; N-methyl-2-pyrrolidone; water, etc. can be referred to.


According to the need, adjuvants can be incorporated into the controller of this invention. As the adjuvants, surfactants, antioxidants, emulsifiers, etc. can be referred to. More specific examples of the adjuvants include surfactants such as polyoxyethylene alkylaryl ether, polyoxyethylene sorbitan monolaurate, alkylaryl sorbitan monolaurate, alkylbenzenesulfonates, alkylnaphthalene-sulfonic acid, ligninsulfonic acid salts, higher alcohol sulfate salts, glycol monoalkyl ethers, glycols, and the like; emulsifiers such as sorbitan monooleate, sorbitan monolaurate, caprylic acid monoglyceride, capric acid monoglyceride, isostearic acid monoglyceride, propylene glycol monocaprylate, etc; and antioxidants such as BHA, BHT, etc.


The ectoparasitic insect pest controller composition for animals of this invention can contain the insect pest controller of this invention as an active ingredient in an amount of 0.01-80.0% by weight per 100 parts by weight of the present composition.


The methods for using the ectoparasitic insect pest controller for animals of this invention include a pot-on treatment which comprises dropping a liquid agent onto the skin of the back shoulder region of the objective animal and thereby controlling the ectoparasitic insect pest; and a local treatment such as pore-on which comprises applying a liquid agent along the back center line of the objective animal and the allowing the applied agent to diffuse on the body surface and thereby controlling the ectoparasitic insect pest; as well as a treatment method of supporting the agent on a collar or the like from which the agent is released; a treatment method of directly coating a liquid agent or an ointment onto the body surface; a treatment method of applying an aerosol of a liquid agent by means of spray or the like; etc. The dose of the agent may be appropriately selected from a range of about 0.1 to 500 mg as expressed in terms of active ingredient compound, and from a range of about 0.01 to 20 ml as expressed in terms of the insect pest controller of this invention, both per kilogram of body weight of the objective animal.


According to the need, the ectoparasitic insect pest controller for animals of this invention may be used in combination with other active ingredients. As said “other active ingredient”, for example, the following can be referred to:

    • pyrethroid compounds such as permethrin, phenothrin, allethrin, pyrethrin, prallethrin, cyphenothrin, cyfluthrin, fenvalerate, fenpropathrin, transfluthrin, etc.;
    • organic phosphorus compounds such as dichlorvos, tetrachlorvinphos, fenthion, chlorpyrifos, diazinon, etc.;
    • N-phenylpyrazole compounds such as fipronil, etc.;
    • carbamate compounds such as propoxur, carbaryl, metoxadiazone, fenocarb, etc.;
    • neonicotinoid compounds; etc.


EXAMPLES
Example 1

















A compound shown in Tables 1-4
 5 parts



Hexylene glycol
50 parts



Isopropanol
45 parts










The above-mentioned ingredients were uniformly mixed and dissolved together to obtain a liquid formulation.


Example 2

















A compound shown in Tables 1-4
10 parts



Polyoxyethylene styrylphenyl ether
10 parts



Cylohexanone
80 parts










The above-mentioned ingredients were uniformly mixed and dissolved together to obtain an emulsifier.


Test Example 1

A spot-on agent was prepared by mixing and dissolving 10 parts by weight of Compound 44 or Compound 96 in 90 parts by weight of diethylene glycol monoethyl ether. One day before the day of administration, 30 fleas [adult worm of cat flea (Ctenocephalides felis)] were made to parasitize a cat, and the cat was let wear an Elizabeth collar on the neck. Then, 0.4 ml of a test agent was applied to the skin of back shoulder area of the cat (alive body weight 3.2 kg). One day after and three days after the treatment using the agent, the number of parasitic fleas was counted by means of a flea-catching comb. After counting the number of parasitic fleas, the whole fleas were again made to parasitize the cat. As a blank test, fleas were made to parasitize an untreated cat in the same manner as above, and the number of parasitic fleas was counted. The controlling rate was calculated according to the following formula, and the result was judged according to the criterion shown below.

















Controlling
⁢

 

⁢
rate
⁢

 

⁢

(
%
)


=







Parasitic
⁢

 

⁢
rate






in
⁢

 

⁢
untreated





group



-




Parasitic
⁢

 

⁢
rate






in
⁢

 

⁢
treated





group








Parasitic
⁢

 

⁢
rate
⁢

 

⁢
in






untreated
⁢

 

⁢
group





×
100















Criterion of judgement
Controlling rate (%)







A
100



B
99-90



C
89-80



D
79-50










Thus, both the ectoparasitic insect pest controllers for animals containing Compound No. 44 and Compound No. 96 of this invention gave a judgement of A.

Claims
  • 1. A method of controlling ectoparasitic insect pests for animals which comprises the steps of administering an effective amount of a controller to the body surface of an animal, which contains, as active ingredient thereof, a hydrazine derivative represented by the following general formula (I):
  • 2. The method of controlling ectoparasitic insect pests for animals according to claim 1, represented by the following general formula (I-1):
  • 3. The method of controlling ectoparasitic insect pests for animals according to claim 1, represented by the following general formula (I-2):
  • 4. The method of controlling ectoparasitic insect pests for animals according to claim 1, represented by the following general formula (I-3):
  • 5. The method of controlling ectoparasitic insect pests for animals according to claim 1, represented by the following general formula (I-4):
  • 6. The method of controlling ectoparasitic insect pests for animals according to claim 1, wherein the active ingredient is present in an amount of 0.01-80.0% by weight.
  • 7. The method of controlling ectoparasitic insect pests for animals according to claim 1, wherein the effective amount is a dose of 0.1 to 500 mg per kilogram of body weight of the animal.
  • 8. The method of controlling ectoparasitic insect pests for animals according to claim 7, wherein the controller includes a liquid carrier and the dose is in an amount of 0.01 to 20 ml of the controller applied per kilogram of body weight of the animal.
Priority Claims (1)
Number Date Country Kind
2000-317887 Oct 2000 JP national
PCT Information
Filing Document Filing Date Country Kind 371c Date
PCT/JP01/09076 10/16/2001 WO 00 5/21/2003
Publishing Document Publishing Date Country Kind
WO02/32226 4/25/2002 WO A
US Referenced Citations (1)
Number Name Date Kind
5543573 Takagi et al. Aug 1996 A
Foreign Referenced Citations (5)
Number Date Country
0462456 Dec 1991 EP
0657421 Jun 1995 EP
5-32603 Feb 1993 JP
5-262712 Oct 1993 JP
WO 0101781 Jan 2001 WO
Related Publications (1)
Number Date Country
20030199579 A1 Oct 2003 US