Ant controllers and method for application thereof

Description

BACKGROUND OF THE INVENTION
Field of the Invention

The present invention relates to novel ant controller containing a hydrazine derivative as an active ingredient and to a method for application of the ant controller.

RELATED ART

The hydrazine derivatives represented by the formula (I) which can be used as active ingredient of the ant controllers of the present invention are known compounds disclosed in JP-A-5-4958, JP-A-5-17428, JP-A-5-32603, JP-A-5-262712, etc. In these patents, it is described that these derivatives have an insecticidal activity as agrihorticultural insecticides against LEPIDOPTERA such as diamondback moth, rice leafroller, etc., HEMIPTERA such as tea green leafhopper, pear lace bug, etc., COLEOPTERA such as twenty-eight-spotted ladybird, maize weevil, etc., DIPTERA such as melon fly, house fly, house mosquito, etc., and TYLENCHIDA such as coffee root-lesion nematode, root-knot nematode, etc.

Any of these patent gazettes, however, does neither describe nor suggest that said hydrazine derivatives have a marked insecticidal effect against ISOPTERA such as formosan subterranean termite, kolbe, etc., HYMENOPTERA such as cabbage sawfly, Carpenter ant, etc., ORTHOPTERA such as Japanese cockroach, field cricket, rice grasshopper, etc., and PSOCOPTERA such as large pale booklouse, etc.

SUMMARY OF THE INVENTION

The present inventors have conducted extensive studies with the aim of creating a novel ant controller having a marked controlling effect upon ants doing harm to the wooden materials constituting houses, furniture, etc. or crops and human being. As a result, it has been found that some of the hydrazine derivatives described in the above-mentioned prior art have a marked insecticidal effect upon termites and ants. The present invention has been accomplished on the basis of this findings.

DETAILED DESCRIPTION OF THE INVENTION

The present invention relates to ant controllers containing as active ingredient thereof a hydrazine derivative represented by the following formula (I) and method for application of the ant controllers:

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wherein A represents:

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(wherein R⁴represents hydrogen atom or C₁-C₆alkyl group, and X represents 1 to 5, same or different substituents selected from the group consisting of hydrogen atom, halogen atom, C₁-C₆alkyl group and halo C₁-C₆alkyl group),

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(wherein R⁴and X are as defined above, and R⁵represents hydrogen atom, C₁-C₆alkylcarbonyl group or phenyl-carbonyl group which may have 1 to 2, same or different substituents selected from the group consisting of C₁-C₆alkyl groups),

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(wherein R⁴and X are as defined above), or

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(wherein R⁴and X are as defined above);

R¹represents hydrogen atom or C₁-C₆alkyl group;

R²and R³, which may be same or different, represent hydrogen atom, hydroxyl group, C₁-C₆alkyl group, C₁-C₆alkoxy group, alkylcarbonyl group or phenylcarbonyl group;

Y represents 1 to 5, same or different substituents selected from the group consisting of hydrogen atom, halogen atom, nitro group and cyano group;

Z represents halogen atom, cyano group, C₁-C₆alkyl group, halo C₁-C₆alkyl group, C₁-C₆alkoxy group, halo C₁-C₆alkoxy group, halo C₁-C₆alkylthio group, halo C₁-C₆alkylsulfinyl group or halo C₁-C₆alkylsulfonyl group; and

W represents oxygen atom or sulfur atom.

The ant controller of the present invention is an excellent ant controller for protecting wooden materials such as trees, board fences, sleepers, etc. and buildings such as shrines, temples, houses, outhouses, factories, etc. from ants such as termites, and for controlling ants doing harm to crops or human being.

In the definition of the formula (I) shown above, the term “halogen atom” means chlorine atom, bromine atom, iodine atom and fluorine atom; the term “C₁-C₆alkyl” means a straight or branched chain alkyl group having 1 to 6 carbon atoms; and the term “halo C₁-C₆alkyl” means an alkyl group having 1 to 6 carbon atoms substituted with at least one, same or different halogen atoms.

Preferable examples of the hydrazine derivative represented by the formula (I) of the present invention are the hydrazine derivatives represented by the formulas (I-1) and (1-2) as mentioned below. Preferable examples of each substituent of the hydrazine derivatives of formulas (I-1) and (1-2) are the compounds wherein W is oxygen atom, X is trifluoromethyl group, Y is cyano group, Z is trifluoromethoxy group, and each of R¹, R², R³and R⁴is simultaneously a hydrogen atom. More preferable examples are the compounds wherein X is substituted on the 3-position, and Y is substituted on the 4-position of the phenyl ring.

Most preferable example is the hydrazine derivative represented by the formula (I-1), wherein each of R¹, R², R³and R⁴is simultaneously a hydrogen atom, X is trifluoromethyl group substituted on the 3-position of the phenyl ring, Y is cyano group substituted on the 4-position of the phenyl ring, and Z is trifluoromethoxy group.

Typical examples of the hydrazine derivative represented by the formula (I) used as an active ingredient of the ant controller of the present invention are shown in Table 1 to Table 4, but the present invention is by no means limited to the compounds exemplified herein.

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TABLE 1

No .
R¹
R²
R³
R⁴
X
Y
Z
W
mp □

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

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

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

Note:

Ph is phenyl group.

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TABLE 2

(R¹and R³are hydrogen atoms)

No.
R²
R⁴
R⁵
X
Y
Z
W
mp □

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

(−)-Iso-

mer

118
H
H
H
3-CF₃
4-CN
OCF₃
O
126

(+)-Iso-

mer

119
H
H
H
3-CF₃
4-CN
SOCF₃
O
Glassy

120
H
H
H
3-CF₃
4-CN
SO₂CF₃
O
Glassy

121
H
H
H
H
3-CN
OCF₃
O
120

Note:

Ph is phenyl group.

Compounds 106 and 107 are diasteromers.

Compound 106 is higher than Compound 107 in the Rf value.

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TABLE 3

(R²and R³are hydrogen atoms, and W is oxygen

atom.)

mp □, Refractive

No
R¹
R⁴
X
Y
Z
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□□

141
CH₃
H
3-CF₃
4-CN
Cl
209-211

142
H
H
3-Cl
2-CN
OCF₃
148

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TABLE 4

(R¹, R², R³and R⁴are hydrogen atoms.)

No
X
Y
Z
mp □, 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□)

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

150
3-Cl
4-NO₂
OCF₃
Viscous

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□)

155
3-CH₃
4-CN
Cl
138-139

156
3-CH₃
4-CN
OCF₃
nD 1.5315 (28□)

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 or glassy substances. Their ¹H-NMR data are summarized in Table 5.

TABLE 5

No

¹H-NMR [CDCl₃/TMS, δ (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 ant controller of the present invention exhibits a markedly high killing effect at a low dosage upon all the termites doing harm to houses, construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables, for example, RHINOTERMITIDAE including Coptotermes formosanus Shiraki, Reticulitermes speratus (Kolbe), Reticulitermes hesperus which inhabits the North America, Reticulitermes tibialis, Reticulitermes flavipes, Reticulitermes lucifugus which inhabits the shore of the Mediterranean, Reticulitermes santonensis, Incisitermes minor (Hagen), TERMITIDAE including Odontotermes formosanus (Shiraki), KALOTERMITIDAE including Cryptotermes domesticus (Haviland), TERMOPSIME including Hodotermopsis japonica (Holmgren), etc.

Further, the ant controller of the present invention exhibits a markedly high killing effect at a low dosage upon all the ants doing harm to crops, or to human being when the ants invade into houses and public facilities such as parks, for example, FORMICIDAE including Monomorium pharaonis Linne, Monomorium nipponense Wheelex, Camponotus kiusiuensis Santschi, Formica japonica Motschulsky, Lasius fuliginosus (Latreille), Solenopsis richteri, Solenopsis invicta, Solenopsis geminata (Fireant), etc.

For using the ant controller of the present invention containing the hydrazine derivative of formula (I) as an active ingredient efficiently, the ant controller is formulated with a proper solid carrier and/or liquid carrier. If necessary, it is formulated with auxiliaries in a proper proportion according to the conventional recipe of formulation, and homogenized together with the carrier by the method of dissolution, suspension, mixing, impregnation, adsorption or adhesion, so as to be made it into an appropriate preparation form such as oily solution, emulsifiable concentrate, solubilized concentrate, dust, granule, wettable powder, aerosol, fumigant, flowable preparation or the like. It is also possible to form the termite controller into a bait preparation by compounding it with a bait containing an attractant or the like.

As the solid carrier used in the present invention, there can be exemplified clays such as kaolin, bentonite, acid clay and the like; talcs such as talc, pyrophillite and the like; silica materials such as diatomaceous earth, siliceous sand, mica, synthetic silicate, synthetic high-dispersion silica and the like; and inorganic mineral powders such as pumice, sand and the like; organic matters such as pieces of wood, chips of pulp wood, grain flour, sugars and the like. As the liquid carrier, there can be exemplified alcohols such as methyl alcohol, ethyl alcohol, ethylene glycol and the like; ketones such as acetone, methyl ethyl ketone, cyclohexanone and the like; ethers such as ethyl ether, dioxane, tetrahydrofuran, Cellosolves and the like; aliphatic hydrocarbons such as light oil, kerosene and the like; aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, cyclohexanone, methylnaphthalene and the like; and halogenated hydrocarbons such as chloroform, carbon tetrachloride, chlorobenzene and the like. These solid and liquid carriers may be used either alone or in the form of a mixture.

As the auxiliaries which can be used in the present invention, surfactants, dispersants, sticking agents, etc. can be referred to. As the surfactants, there can be exemplified polyoxyethylene alkylaryl ethers, polyoxyethylene sorbitan monolaurates, alkylaryl sorbitan monolaurates, alkylbenzesulfonates, alkylnaphthalene-sulfonates, ligninsulfonates, higher alcohol sulfuric ester salts, etc. These surfactants may be used either alone or in the form of a mixture.

As the dispersants or sticking agents, for example, casein, gelatin, starch, alginic acid, carboxymethyl cellulose, agar, polyvinyl alcohol, turpentine oil, etc. can be used according to the need.

The ant controller of the present invention is applied not only to the surrounding soil surface or into the under-floor soil in order to protect wooden materials such as trees, board fences, sleepers, etc. and structures such as shrines, temples, houses, outhouses, factories, etc., but it can also be applied to lumbered articles such as surfaces of the under-floor concrete, alcove posts, beams, plywoods, furniture, etc., wooden articles such as particle boards, half boards, etc. and vinyl articles such as coated electric wires, vinyl sheets, heat insulating material such as styrene foams, etc. In case of application against ants doing harm to crops or human beings, the ant controller of the present invention is applied to the crops or the surrounding soil, or is directly applied to the nest of ants or the like.

The present invention is not limited to the embodiments mentioned above, but it also includes the embodiments of applying the ant controller of the invention preventively to places at which occurrence of ants is expected.

In putting the ant controller of the present invention, the dosage may be appropriately selected from the ranges properly chosen. In case of application to wooden materials, the quantity of active ingredient ranges from 0.1 to 50 g per m²; and in case of soil treatment or application to the nests, the quantity of active ingredient ranges from 1 to 500 g per m².

EXAMPLES

Next, typical examples and test example of the present invention are presented below. The invention is by no means limited to these examples.

In the examples, “parts” are by weight.

Formulation Example 1

Each hydrazine derivative listed
20 parts

in Tables 1-4

Xylene
80 parts

The ingredients mentioned above were made into a uniform solution to obtain an oily solution.

Formulation Example 2

Each hydrazine derivative listed
10 parts

in Tables 1-4

Polyoxyethylene styrylphenyl ether
10 parts

Cyclohexanone
80 parts

The ingredients mentioned above were uniformly mixed and dissolved together to obtain an emulsifiable concentrate.

Formulation Example 3

Each hydrazine derivative listed
10 parts

in Tables 1-4

Sodium alkylbenzenesulfonate
2 parts

White carbon
10 parts

Clay
78 parts

The ingredients mentioned above were uniformly mixed and pulverized to obtain a wettable powder.

Formulation Example 4

Each hydrazine derivative listed
8 parts

in Tables 1-4

Cyclohexanone
4 parts

Mixture of polyoxyethylene nonylphenyl
3 parts

ether and alkylbenzenesulfonic acid

A granular composition was prepared by uniformly mixing and dissolving together the ingredients mentioned above, and spraying the resulting solution onto 85 parts of granular pumice, followed by drying.

Test Example 1

A filter paper was spread in a glass dish having a diameter of 9 cm, onto which was dropped 1 ml of a 500 ppm solution of the ant controller of the present invention. Then, the filter paper was inoculated with Coptotermes formosanus Shiraki. Seven days after the inoculation, percentage of dead insects was investigated, from which mortality was calculated. The results were evaluated according to the following criterion. The test was carried out with triplicate group of 10 insects.

Criterion
Mortality (%)

A
100

B
99-90

C
89-80

D
79-50

The results are summarized in Table 6.

TABLE 6

Compound
Termite-killing

No.
effect

1
A

2
B

3
A

4
A

5
A

6
A

7
A

8
C

9
B

10
A

11
A

12
A

13
A

14
A

15
B

16
C

17
A

18
A

19
A

20
A

21
A

22
B

23
A

24
C

25
D

26
A

27
A

28
C

29
C

30
A

31
A

32
A

33
C

34
A

35
A

36
B

37
A

38
B

39
A

40
D

41
A

42
A

43
A

44
C

45
A

46
A

47
A

48
A

49
C

50
A

51
A

52
A

53
B

54
A

55
A

56
A

57
D

58
A

59
C

60
C

61
A

62
A

63
A

64
A

65
C

66
A

67
A

68
A

69
B

70
A

71
A

72
A

73
A

74
A

75
A

76
A

77
A

78
A

79
B

80
A

81
A

82
B

83
D

84
A

85
C

86
A

87
C

88
A

89
B

90
A

91
A

92
A

93
D

94
A

95
A

96
A

97
A

98
A

99
A

100
A

101
A

102
A

103
A

104
A

105
B

106
A

107
D

108
C

109
C

110
B

111
D

112
A

113
A

114
B

115
A

116
B

117
A

118
D

119
A

120
A

121
C

122
D

123
A

124
D

125
A

126
A

127
A

128
A

129
A

130
C

131
C

132
A

133
A

134
A

135
B

136
A

137
A

138
A

139
A

140
A

141
D

142
C

143
C

144
B

145
A

146
D

147
A

148
A

149
A

150
C

151
C

152
B

153
A

154
B

155
A

156
B

157
A

158
C

Test Example 2

The ant controller of the present invention was applied to nests (anthill) of fireant (Solenopsis geminata) with drench treatment, in terms of 1 g of the active ingredient per one nest. 14 Days after the treatment of the ant controller, the activity of the nests was evaluated according to the following criterion. The test was carried out with one block per one nest.

Criterion
Effect

A
Nest is completely destructed or

activity of the nest is extremely low.

B
Activity of the nest is exhibited.

C
High activity of the nest is

exhibited.

D
Activity of the nest is extremely

high.

As a result of the test, compound Nos. 44 and 96 of the present invention exhibited the effect “A”.

Claims

1. A method for controlling a pest selected from the Isoptera and Hymenoptera orders which comprises applying to the pest or to a wooden part or to soil in the habitat of the pest an effective amount of a hydrazine compound of formula (I-1):
2. The method of claim 1, wherein the hydrazine compound is applied to the wooden part and the pest is selected from the Rhinotermitidae, Termitidae, Kalotermitidae and Termopsidae families.
3. The method of claim 1, wherein X is trifluoromethyl and Z is trifluoromethoxy.
4. The method of claim 3, wherein Y is 4-cyano.
5. The method of claim 1, wherein the hydrazine compound is applied to the pest.
6. The method of claim 1, wherein the pest is an ant or a termite.
7. A method for protecting houses or an article selected from construction materials, furniture, leather, fibers, vinyl articles, electronic wires and cables against a pest selected from the Rhinotermitidae, Termitidae, Kalotermitidae and Termopsidae families, which comprises applying an effective amount of a hydrazine compound of formula (I-1):
8. The method of claim 7, wherein X is trifluoromethyl, Y is 4-cyano, and Z is trifluoromethoxy.
9. The method of claim 7, wherein the hydrazine compound is applied to the pest.
10. A method for controlling a pest from the Formicidae family in crops, which comprises applying an effective amount of a hydrazine compound of formula (I-1):
11. The method of claim 10, wherein X is trifluoromethyl, Y is 4-cyano, and Z is trifluoromethoxy.
12. The method of claim 10, wherein the hydrazine compound is applied to the pest.
13. A method for protecting wooden materials from termites and ants which comprises applying an effective amount of a hydrazine compound of formula (I-1):
14. A method for protecting crops from pests of the Formicidae family which comprises applying an effective amount of a hydrazine compound of formula (I-1):
15. A method for controlling a pest selected from ants and termites of the Isoptera and Hymenoptera orders which comprises applying to the pest or a nest of the pest, or to a wooden part or to soil in the habitat of the pest, an effective amount of a hydrazine compound of formula (I-1):
16. The method of claim 15, wherein the pest is a termite from the Rhinotermitidae, Termitidae, Kalotermitidae or Termopsidae family, or is an ant from the Formicidae family.
17. The method of claim 15, wherein the pest is a termite from the Rhinotermitidae, Termitidae, Kalotermitidae or Termopsidae family.
18. The method of claim 15, wherein the pest is an ant from the Formicidae family.
19. The method of claim 15, wherein the hydrazine compound of formula (I-1) is applied to the pest in form of a bait preparation.
20. The method of claim 15, wherein the mortality is at least 80%.
21. The method of claim 15, wherein X is a trifluoromethyl group and Y is a trifluoromethoxy group.
22. The method of claim 21, wherein X is in the 3-position of the phenyl ring and Y is in the 4-position of the phenyl ring.
23. A method for protecting a house or an article selected from construction materials, furniture, leather, fibers, vinyl articles, electronic wires and cables against a termite selected from the Rhinotermitidae, Termitidae, Kalotermitidae and Termopsidae families, which comprises applying an effective amount of a hydrazine compound of formula (I-1):
24. The method of claim 23, wherein the hydrazine compound of formula (I-1) is applied to the termite in form of a bait preparation.
25. The method of claim 23, wherein X is a trifluoromethyl group and Y is a trifluoromethoxy group.
26. The method of claim 25, wherein X is in the 3-position of the phenyl ring and Y is in the 4-position of the phenyl ring.
27. A method for controlling an ant from the Formicidae family in crops, which comprises applying an effective amount of a hydrazine compound of formula (I-1):
28. The method of claim 27, wherein the hydrazine compound of formula (I-1) is applied to the ant in form of a bait preparation.
29. The method of claim 27, wherein the mortality is at least 80%.
30. The method of claim 27, wherein X is a trifluoromethyl group and Y is a trifluoromethoxy group.
31. The method of claim 30, wherein X is in the 3-position of the phenyl ring and Y is in the 4-position of the phenyl ring.

Priority Claims (1)

Number	Date	Country	Kind
11-190671	Jul 1999	JP	national

PCT Information

Filing Document	Filing Date	Country	Kind	371c Date
PCT/US00/17895	6/28/2000	WO	00	4/4/2002

Publishing Document	Publishing Date	Country	Kind
WO01/01781	1/11/2001	WO	A

US Referenced Citations (5)

Number	Name	Date	Kind
5484599	Yoder et al.	Jan 1996	A
5543573	Takagi et al.	Aug 1996	A
5691383	Thoms et al.	Nov 1997	A
5886221	Sbragia et al.	Mar 1999	A
6342518	Treacy et al.	Jan 2002	B1

Foreign Referenced Citations (2)

Number	Date	Country
0500111	Aug 1992	EP
9206076	Apr 1992	WO

Non-Patent Literature Citations (3)

Entry
Metcalf. Destructive and Useful Insects p. 186,187, 1976.
Metcalf et al. Destructive and Useful Insects p. 186,187, 1962.
Stefferud, ed, Insects—the year book of agriculture, p. 469-1952.

Ant controllers and method for application thereof

Information

Patent Number

Date Filed

Date Issued

Inventors

Original Assignees

Examiners

Agents

CPC

US Classifications

Field of Search

US

International Classifications

Term Extension

Abstract

Description

Claims

Priority Claims (1)

PCT Information

US Referenced Citations (5)

Foreign Referenced Citations (2)

Non-Patent Literature Citations (3)