SK19372000A3 - Use of hydrazine derivatives for killing pests - Google Patents

Abstract

There is disclosed the use of hydrazine derivative of the general formula (I) for controlling pest being selected from strains consisting of Isoptera, Hymenoptera, Orthoptera and Psocoptera., and for the use for fighting pest of the Rhinotermitidae, Termitidae, Kalotermitidae, Termopsidae and Formicidae family.

Description

Use of hydrazine derivatives for pest control

Technical field

The invention relates to the use of hydrazine derivatives for pest control.

BACKGROUND OF THE INVENTION

The hydrazine derivatives of the formula I which can be used according to the invention are known from EP-A 462 456 and EP-A 486 937. These documents state that these derivatives exhibit insecticidal activity as agricultural insecticides for horticulture against Lepidoptera, such as cabbage whitefish, rice dresser, Hemiptera such as cicada, pear reticulate, Coleoptera such as 28-spotted ladybug, corn carrier, Diptera such as watermelon, house fly, mosquito and Tylenchida such as peacock coffee tree, root nematode.

However, it is not known that the hydrazine derivatives of the formula I have a considerable insecticidal effect.

SUMMARY OF THE INVENTION

The invention relates to the use of hydrazine derivatives of the general formula (I)

where

R ¹ is hydrogen or C 1 -C ₆ -alkyl;

R ² and R ³ which may be the same or different, are hydrogen, hydroxyl, or a C _r C ₆ alkyl group, C -C alkoxy, C -C alkylcarbonyl or phenylcarbonyl;

And it means

• · r e r e

where

R ⁴ represents hydrogen or C 1 -C ₆ -alkyl; and

X represents 1 to 5 same or different substituents, which may be hydrogen, halogen, _Cl-C6 alkyl group and a C -C ₆ -halo-alkyl;

or.

N (R 1 -N (R wherein R ⁴ and X are as defined above);

R ⁵ is a _C-C -alkylcarbonyl or phenylcarbonyl which may have 1 or 2 identical or different Ci-C ₆ -alkyl substituent;

or church ⁴ ) = nn -? wherein R ⁴ and X are as defined above; or or

wherein R ⁴ and X are as defined above; and

Y represents 1 to 5 identical or different substituents which may be hydrogen, halogen, nitro or cyano;

Z is halogen, cyano, C iC-al ₆ alkyl group, C ^ -C haloalkyl, C -C alkoxy group, -halogénalkoxylovú -C ₆ alkyl, C ₆ -C -halogénalkyltioskupinu, C ₆ or a group -halogénalkylsulfinylovú CPCE -haloalkylsulfonyl; arreo r. C

-3 C rr <· * t C C C o .r <

n r c c r 6υ ii '- yy- yyy · · - <- yyyy- · yyyy

W represents oxygen or sulfur;

for the control of pests selected from the series Isoptera, Hymenoptera, Orthoptera and Psocoptera.

The invention also relates to the use of the compounds of formula I as defined above for the protection of wood materials against pests of the family Rhinotermitidae, Termitidae, Kalotermitidae and Termopsidae.

It is an object of the present invention to provide a method for controlling Isoptera, Hymenoptera, Orthoptera and Psocoptera pests.

It is an object of the present invention to provide a method for protecting wood materials from pests of the family Rhinotermitidae, Termitidae, Kalotermitidae and Termopsidae.

We have found that this objective can be achieved using the compounds defined in the introduction. In addition, we have found the use of the compounds of formula I for pest control as defined in the introduction.

The present invention provides a new method of destroying ants causing damage to wood materials used for houses, furniture, and the like or agricultural crops and humans. The hydrazine derivatives of the formula I have been found to have a considerable insecticidal effect on termites and ants.

However, it is not known that the hydrazine derivatives of the formula I have a considerable insecticidal activity against Isoptera, such as oak and others. others, and Psocoptera, such as pale spiders and others.

'' I

The compounds of formula I may be used to protect wood materials such as trees, wooden fences, thresholds, and the like, and buildings such as shrines, churches, houses, farm buildings, plants and the like, from ants and termites, and to destroy ants harmful to crops and humans.

In the definition of Formula I above, the term halogen means chlorine, bromine, iodine and fluorine; the term C 1 -C 6 -alkyl means a straight or branched chain alkyl group having 1 to 6 carbon atoms and the term f e r f r r

(C 1 -C 6 -halo-haloalkyl) means an alkyl group having 1 to 6 carbon atoms substituted with at least one, same or different halogen atoms.

Preferred examples of the hydrazine derivative represented by Formula I of the present invention are the hydrazine derivatives represented by Formulas I1 and I-2 as shown below. Preferred examples of each substituent of the hydrazine derivatives of formulas 1-1 and I-2 are compounds wherein W is oxygen, X is trifluoromethyl, Y is cyano, Z is trifluoromethoxy and each of R ¹ , R ² , R ³ and R ⁴ is hydrogen at the same time.

More preferred examples are compounds of formula I wherein X is substituted at the 3-position and Y is substituted at the 4-position of the phenyl ring.

The most preferred example is a hydrazine derivative represented by formula I1, wherein each of R ¹ , R ² , R ³ and R ^{4 is} simultaneously hydrogen, X represents a trifluoromethyl group substituted at the 3-position of the phenyl ring, Y represents a cyano group substituted at the 4-position of the phenyl ring. trifluoromethoxy group.

Typical examples of the hydrazine derivative represented by formula I used in the present invention are shown in Tables 1 to 4, but the present invention is by no means limited to the compounds exemplified.

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r * o rH (β 0 • HC (D> O '3 rH • N> 1 • MO g' Φ A4 CE d • rl O 04 N 0 0 -HPA! OO ω Q) c M -Ú '0 φ o > px O tn P <0 P> ir | Pi 0 Ό <D 0 P '0 -H tn> tn' (0> to 0 r-> i ω o> EH <tJ 'tts 0, EN in X oo rH rH ··> 1 <0 <0 0 0 X -H -HE 0 0 '<D (DQ) 0> υ> υ N' 0 '0 OHH fa CO CO

-12Table 3. ,,.

In formulas 1-3, R and R are hydrogen and W is oxygen

(1-3)

Č - R ¹ R ⁴ X Y FROM tt (° _{C) /} refractive index 122 H H H H OCF ₃ 113.3 to 114.0 123 H H H 4-C1 ocf ₃ 137.8 124 H H H 4-CN Cl 163 125 H H H 4-CN OCF ₃ 138 126 H H 3-C1 4-C1 Cl 143.5 to 144.0 127 H H 3-C1 4-C1 OCF ₃ 139.6 to 141.5 128 H H 3-C1 4-NOZ Cl 174.0-176.5 129 H H 3-C1 4-NOZ OCF ₃ 151.6 to 151.7 130 H H 3-C1 4-CN Cl 191.0 to 192.0 131 H H 3-C1 4-CN OCF ₃ 160.5 to 162.0 132 H H 3-C1 4-CN scf ₃ 188.0 133 H H 3-C1 4-CN socf ₃ 206.1 134 H H 3-F 4-CN Cl 154-156 135 H H 3-F 4-CN 0CF3 155.9 to 156.8 136 H H 3-CH ₃ 4-CN Cl 127 137 H H 3-CH ₃ 4-CN ocf ₃ 166 138 H H 3-CF ₃ 4-CN Cl 164-165 139 H H 3-CF ₃ 4-CN 0CF3 151.0 140 H CH ₃ 3-C1 4-CN 0CF3 n _D 1.5950 (25 ° C) 141 ch ₃ H 3-CF ₃ 4-CN Cl 209-211 142 H H 3-C1 2-CN OCF 3 148

-13r yy r

Table 4 i 2 3 4

In formulas 1-4, R, R, R and R are hydrogen

č · X y FROM t. (° C), refractive index 14 3 H H OCF 3 51.0 to 53.0 144 H 4-C1 OCF 3 92.1 145 H 4-CN Cl 106-108 146 H 4-CN OCF 3 n _and 1,5685 (27®C) 147 3-Cl 4-C1 Cl 105.3 to 106.4 148 3-Cl 4-C1 ocf ₃ 38.0 149 3-Cl 4-NO 2 Cl viscous 150 3-Cl 4-NO ₂ OCF 3 viscous 151 3-Cl 4-CN Cl 153.1 152 3-Cl 4-CN OCF 3 43.5 to 45.0 153 3-F 4-CN Cl 164-165 154 3-F 4-CN OCF 3 n _D 1.5615 (27 ° C) 155 3-CH ₃ 4-CN Cl 138-139 156 3-CH3 4-CN OCF 3 n _D 1.5315 (28 ° C) 157 3-CF3 4-CN Cl 43 158 3-CFj 4-CN OCF 3 153.1

Some of the compounds listed in Tables 1 to 4 are viscous or vitreous.

C Λ t c r r <r

The -14Ich H-NMR data are summarized in Table 5:

no. 1 H-NMR [CDCl ₃ / TMS, δ (ppm)] 59 6.29 (s, 1H); 7.65-7.92 (m, 13H); 9.14 (bs, 1H); 10.70 (bs, 1H). (Di-iso-d) 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, IH); 4.12-4.32 (m, 2 H); 6.13 (bs, 1H); 7.24-7.93 (m, 12H); 8.08 (bs, 1 H). 120 3.11 (dd, 1H); 3.23 (dd, 1H); 4.13-4.28 (m, 2 H); 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, 2 H); 6.85 (dd, 1H); 6.93 (dd, 1H); 7.08 (dd, 1H); 7.15-7.21 (m, 3H); 7.24 (d, 2 H); 7.40 (d, 2 H); 8.13 (d, 2 H); 8.40 (s, 1H). 150 3.64 (s, 2 H); 4.69 (s, 2 H); 6.84 (dd, 1H); 6.94 (dd, 1H); 7.09 (m, 3H); 7.23 (t, 1H); 7.29 (d, 2 H); 7.40 (d, 2 H); 8.12 (d, 2 H); 8.40 (s, 1H).

f c c e e * c t ·

The compounds of formula I exhibit a considerably high low-dose killing effect for all termites that are harmful to houses, construction materials, furniture, leather, fibers, vinyl products, electrical wires and cables such as Rhinotermitidae, including Coptotermes formosanus Shiraki, Reticulitermes speratus ( Kolbe), Reticulitermes hesperus, living in North America, Reticulitermes tibialis, Reticulitermes flavipes, Reticulitermes lucifugus, living on the Mediterranean coast, Reticulitermes santonensis, Incisitermes minor (Hagen), Termitidae, domesticus (Haviland), Termopsidae, including Hodotermopsis Japonica (Holmgren), and others.

In addition, the ant regulators of the present invention exhibit a considerably high low dose killing effect for all ants that are harmful to agricultural crops or humans if the ants attack houses and public facilities such as parks such as Formicidae, including Monomorium pharaonis Linne, Monomorium Wheelex nipponense, Camponotus kiusiuensis Santschi, Motschulsky Formica, Lasius fuliginosus (Latreille), Solenopsis richteri, Solenopsis invicta, Solenopsis geminata (Fireant), and the like.

For use, the hydrazine derivatives of the formula I for controlling pests selected from the series Isoptera, Hymenoptera, Orthoptera and Psocoptera according to the present invention are treated using a suitable solid carrier and / or liquid carrier. If desired, they may be formulated with the adjuvants in an appropriate proportion using conventional treatment regulations and homogenized with the carrier by means of dissolution, suspension, mixing, impregnation, adsorption or adhesion processes to form a suitable formulation such as is an oil solution, emulsifiable concentrate, soluble concentrate, dust, granules, wettable powder, aerosol, smoke, liquid preparation or the like. It is also possible to formulate the compounds of Formula I into baits by compounding them with bait containing bait or the like.

As the solid carrier used in the present invention, for example, clays such as kaolin, bentonite, acid clays and the like; talc such as talc, pyrophyllite and the like; siliceous materials such as diatomaceous earth, silica r r r r

Sand, mica, synthetic silicates, synthetic highly disperse silica and the like; and inorganic mineral powders such as pumice, sand and the like; organic materials such as wood chips, pulp, grain, flour, sugar and the like As the liquid carrier, for example, alcohols such as methanol, ethyl alcohol, ethylene glycol and the like can be used, ketones such as acetone, methyl ethyl ketone, cyclohexanone and the like ethers such as ethyl ether 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, etc. These solid and liquid carriers can be used either alone or in the form of a mixture.

As the auxiliaries which can be used according to the present invention there may be mentioned surfactants, dispersants, tackifiers and the like. As the surfactants, for example, polyoxyethylene alkyl aryl ethers, polyoxyethylene sorbitan monolaurates, alkylarylsorbitan monolaurates, alkylbenzenesulfonates, alkylnaphthalenesulfonates, lignosulfonates, ester salts of sulfuric acid with higher alcohols and the like can be used. These surfactants can be used either alone or in the form of a mixture.

As dispersants or tackifiers, for example, casein, gelatin, starch, alginic acid, carboxymethylcellulose, agar, polyvinyl alcohol, turpentine oil and the like can be used as appropriate.

The compounds of the formula I according to the present invention are applied not only to the surrounding soil surface or to the ground below ground to protect wooden materials such as trees, wooden fences, thresholds and the like, and buildings such as shrines, churches, houses, farms. buildings, factories and the like, but may also be applied to construction products such as underfloor concrete surfaces, alcove spots, laminates, plywood, furniture and the like; wood products such as particle board, laths and the like, and vinyl products such as coated electrical wires, vinyl records, thermal insulating materials such as styrene foams and the like. In case of use against ants that are harmful to agricultural crops or to humans, the ants regulator of the present invention is applied to

-17e e e «r

r c

o e e

r n

c r r e e r r e e r r c c r.,. ' c • r rt. crops or surrounding soil or directly applied to an ants' nest or the like.

The present invention is not limited to the above embodiments, but also encompasses embodiments of the application of the ant regulator of the invention preventively to the sites where ants are expected to occur.

When administering the compounds of formula (I) of the present invention, the dosage may preferably be selected from suitably selected ranges. When used for wood materials, the amount of active ingredient is in the range of 0.1 to 50 g per m ² ; and in the case of soil treatment or nesting, the amount of active ingredient ranges from 1 to 500 g per m ² .

DETAILED DESCRIPTION OF THE INVENTION

The following are typical examples and examples of formulation tests. The invention is by no means limited to these examples.

In the examples, parts are parts by weight.

Example 1 of the formulation

Each hydrazine derivative listed in Tables 1-4

Xylene parts parts

The above ingredients were made into a homogeneous oil solution.

solution to obtain

Example 2 of the formulation

Each hydrazine derivative listed in Tables 1-4

polyoxyethylene styryl

Cyclohexanone parts parts parts

The above ingredients were mixed uniformly and dissolved with each other to obtain an emulsifiable concentrate.

Each hydrazine derivative listed in Tables 1-4

Sodium alkylbenzenesulfonate parts parts

Example 3 of the formulation of the formulation

-18f ee · e · rf> o r c f r

White carbon black clay parts

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

Example 4 of the formulation

Each hydrazine derivative listed in Tables 1-4 8 parts

Cyclohexanone 4 parts

A mixture of polyoxyethylenenonylphenyl ether and alkylbenzenesulfonic acid 3 parts

The granular composition was prepared by uniformly mixing and co-dissolving the above ingredients and spraying the resulting solution on 85 parts of granular pumice stone followed by drying.

Example 1 test

The filter paper was spread in a 9 cm diameter glass dish, to which 1 ml of a 500 ppm solution of the compound of formula I was added dropwise. The filter paper was then seeded with Coptotermes formosanus Shiraki.

Seven days after inoculation, the percentage of dead insects from which mortality was calculated was determined. The results were evaluated according to the following criteria. The test was performed with a triple group of 10 insect individuals.

criterion mortality A 100 B 99-90 C 89-80 D 79 -50

r r r c r se

-19r r c r

The results are summarized in Table 6:

Compound No. Effect of killing termites Compound No. - / ....... ...... termite killing termites 1 A 5 A 2 B 6 A 3 A 7 A 4 A 8 C 9 B 32 A 10 A 33 C 11 A 34 A 12 A 35 A 13 A 36 B 14 A 37 A 15 B 38 B 16 C 39 A 17 A 40 D 18 A 41 A 19 A 42 A 20 A 43 A 21 A 44 C 22 B 45 A 23 A 46 A 24 C 47 A 25 D 48 A 26 A 49 C 27 A 50 A 28 C 51 A 29 C 52 A 30 A 53 B 31 A 54 A 55 A 78 A 56 A 79 B 57 D 80 A 58 A 81 A 59 C 82 B 60 C 83 ' D 61 A 84 A 62 A 85 C 63 A 86 A 64 A 87 C 65 C 88 A 66 A 89 B 67 A 90 A 68 A 91 A 69 B 92 A 70 A 93 D

yy yy yy yy

-20c r

Compound No. Effect of killing termites Compound No. Effect of killing termites 71 A 94 A 72 A 95 A 73 A 96 A 74 A 97 A 75 A 98 A 76 A 99 A 77 A 100 A 101 A 124 D 102 A 125 A 103 A 126 A 104 A 127 A 105 B 128 A 106 A 129 A 107 D 130 C 108 C 131 C 109 C 132 A 110 B 133 A 111 D 134 A 112 A 135 B 113 A 136 A 114 B 137 A 115 A 138 A 116 B 139 A 117 A 140 A 118 D 141 D 119 A 142 C 120 A 143 C 121 C 144 B 122 D 145 A 123 A 146 D 147 A 153 A 148 A 154 B 149 A 155 A 150 C 156 B 151 C 157 A 152 B 158 C

r «c e r r r

-21 e r r f f.

Example 2 test

The compounds of formula I were applied to the nest (anthill) of Solenopsis germinata by soaking in an amount of 1 g of active ingredient per nest. 14 days after treatment, nest activity was evaluated according to the following criteria. The test was performed with one block per nest.

criterion effect A The nest is completely destroyed or the activity of the nest is extremely low. B Demonstrate nest activity. C It shows high nest activity. D Nest activity is extremely high.

As a result of the test, compounds no. 44 and 96 of the present invention showed an effect of "A".

Claims (10)

PATENT REQUIREMENTS e e c * r r r Use of hydrazine derivatives of the general formula I z Υ (dewhere) R ¹ is hydrogen or C 1 -C 6 -alkyl; R ² and R ^3, which may be the same or different, represent hydrogen, hydroxyl, or C ₁ -C ₆ -alkyl, C 1 -C ₆ -alkoxy, C 1 -C ₆ -alkylcarbonyl or phenylcarbonyl; And it means N (R ⁴ ) - n = C 6 where R ⁴ represents hydrogen or C 1 -C ₆ -alkyl; and X represents 1 to 5 same or different substituents, which may be hydrogen, halogen CRCG-alkyl and -C ₆ -haloalkyl group; or N (R ⁴ ) -N (R ⁵ ) -CH- wherein R ⁴ and X are as defined above; and R ⁵ represents C 1 -C 6 -alkylcarbonyl or phenylcarbonyl, which may contain 1 or 2 identical or different C 1 -C ₆ -alkyl substituents; or x r λ r r e e Wherein R ⁴ and X are as defined above; and or wherein R ⁴ and X are as defined above; and Y represents 1 to 5 identical or different substituents which may be hydrogen, halogen, nitro or cyano; Z is halogen, cyano, Ci-C ₆ alkyl group, -C ₆ -haloalkyl, trickle-alkoxy, trickle-haloalkoxy, Ci-Ce-haloalkylthio, -halogénalkylsulfinylovú -C ₆ group or a C ₆ -C -halogénalkylsulfonylovú group; and W represents oxygen or sulfur; for the control of pests selected from the series Isoptera, Hymenoptera, Orthoptera and Psocoptera. Use, according to claim 1, of hydrazine derivatives of the formula I-1 y (M), where the variables are as defined in formula I, The use, according to claim 1, of hydrazine derivatives of formula I-2 (I-2), wherein the variables are as defined in formula I. The use, according to claim 1, of the hydrazine derivatives of the formula I-3 rc-rc e r r o c r o -24r t c o where the variables are as defined in formula I. The use, according to claim 1, of hydrazine derivatives of the formula I-4 z w R ² , II. I N (R ¹ ) —C — CH (R ⁴ ) —NH — N — CR Y x where the variables are as defined in formula I. Use according to claims 1 to 5, wherein the pests are Rhinotermitidae, Termitidae, Kalotermitidae, Termopsidae and Formicidae. elected from the family Use of hydrazine derivatives according to any one of claims 1 to 5 for the protection of wood materials against pests of the family Rhinotermitidae, Termitidae, Kalotermitidae and Termopsidae. Use according to claim 7, wherein the hydrazine derivative is represented by formula 1-1 as defined in claim 2. A method for controlling pests selected from the series Isoptera, Hymenoptera, Orthoptera and Psocoptera, characterized in that a pesticidally effective amount of a hydrazine derivative of the formula I according to claim 1 is applied. A method for the protection of wood materials against pests of the family Rhinotermitidae, Termitidae, Kalotermitidae and Termopsidae, characterized in that a pesticidally effective amount of a hydrazine derivative of the formula I according to claim 1 is applied.