JPS5828249B2 - insecticide, acaricide - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to certain novel pyridazinyl (thiono) (thiol) phosphoric acid esters and ester-amides, processes for their preparation and their use as insecticides and acaricides. It is about use.

0.O-dialkyl-〇-pyridazinyl-thionophosphate, e.g. 0-1:1-phenyltro-dihydro-6-oxtupyridazinyl(3)], 0-(1-hydroxymethyl- 1,6-dihydro-6-oxopyridazin(3)-1-(1-(N-N-dimethylaminomethyl)-i,6-dihydro-6-oxopyridazin43)- and 0(1-(p-methylphenyl)-1
- It is known that 6-dihydro-6-oxopyridazine(3)-0.0-diethylthionolinate has insecticidal and acaricidal properties [US Pat. No. 2,759,937] No. 20025, published patent application
/72 and Journal of Organic Chem.
istry), Volume 26, 1. =1 (1961,),
See pages 3382-3386].

The present invention provides novel compounds with the general formula: is 1-3 alkylthio, R' and R"' may be the same or different and each is hydrogen or methyl, and RIV is chlorine, nitro or trifluoromethyl, and n is O or 1, and X is oxygen or sulfur.

It has been found that compounds of formula (I) have strong insecticidal and acaricidal properties.

The present invention also relates to the general formula [wherein R, 1? and X have the meanings given above, and Hal is halogen. 1-phenyl-3-hydroxy-1,6-sihydropyridazinone (6) derivative of Also provided is a method for preparing a pyridazinyl (thiono) (thiol) phosphonic acid ester or ester-amide of formula (I), wherein

Surprisingly, pyridazinyl (thiono) according to the invention
(thiol) phosphate (phosphonic acid) esters and ester-amides are better insecticides than hitherto known 0,0-diethyl-〇-pyridazinyl-thiophosphate ester derivatives having a similar structure and the same type of activity. and exhibits acaricidal activity.

The novel compounds are not only active against insects and mites that harm plants, but also against pests harmful to health and pests of stored crops, and in the field of veterinary medicine against external parasites of animals, e.g. It is also active against the larvae of the insects.

They are therefore of benefit to the industry.

For example, as starting materials 〇-ethyl〇-secondary-butyl-thionophosphate diester chloride and 1-
(3-5-bis-trifluoromethylphenyl)-3-
When using hydroxy-6-oxopyridazine, the reaction process is represented by the following reaction formula: (thiono)(thiol)phosphonic acid ester halide and ester-amide halide (II) are known; and can be prepared according to methods described in the literature, 1-phenyl-3-hydroxy-drodihydro-
The 6-oxo-pyridazine derivative can be prepared, for example, from a correspondingly substituted phenylhydrazine dissolved in dilute hydrochloric acid by reaction with maleic anhydride according to the formula: [where RIV and n are with the above meaning].

The process for preparing compounds according to the invention is preferably carried out in the presence of a suitable solvent or diluent.

Substantially all inert organic solvents are suitable for this purpose, especially aliphatic and aromatic optionally chlorinated hydrocarbons, such as benzene, toluene, xylene, benzine, methylene chloride, chloroform.

Carbon tetrachloride and chlorobenzene; ethers such as diethyl ether, dibutyl ether and dioxane; ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone; and nitriles such as acetonitrile and propionitrile can be used.

All common acid binders can be used as acid acceptors.

Alkali metal carbonates and alcoholates, such as sodium carbonate, potassium carbonate.

Sodium methylate and ethituate and potassium methylate and ethituate, as well as aliphatic, aromatic or heterocyclic amines such as triethylamine, trimethylamine, dimethylaniline, dimethylbenzylamine and pyridine have proven particularly suitable. .

The reaction temperature can be varied within a fairly wide range.

Generally the reaction is carried out at 0-120<0>C, preferably 40-60<0>C.

To carry out the process, the starting compounds are used in most cases in equimolar amounts.

Excess of either reactant provides no substantial advantage.

The reaction is preferably carried out in the presence of one of the solvents mentioned above, optionally in the presence of an acid acceptor, at the indicated temperature.

After a reaction time of from 1 to several hours, often at elevated temperature, the reaction batch is cooled to room temperature, an organic solvent such as toluene is added, and the organic phase is separated according to general methods.
Treatment, for example, by washing, drying and distillation.

New compounds are often obtained in the form of oils and they cannot be distilled with little decomposition, but the so-called "slight distillation"
That is, the last volatile components can be removed by heating under reduced pressure and at moderately elevated temperatures for a long period of time, and it can be purified in this way.

Refractive index is used to identify these compounds.

Some of the products are obtained in crystalline form, in which case the compound is fixed by its melting point.

As mentioned above, pyridazinyl (thiono) (thiol) phosphoric acid (phosgenic acid) esters and ester-
Amides are characterized by excellent insecticidal and acaricidal activity.

They are active not only against plant pests, health-damaging pests and stored crop pests, but also against animal parasites (ectoparasites) 1, e.g. parasitic fly larvae, in the field of veterinary medicine. It is also active.

They combine low phytotoxicity and good activity against sucking and masticating insects and mites.

For this reason, the compounds according to the invention can be successfully used as insecticides in the field of plant protection and hygiene, in the field of protection of stored crops and in the veterinary field.

Pests of economic importance in agrochemicals and forestry, as well as pests of stored crops, pests destroying materials and harmful to health, include: Isopoda
), such as Yescus Asellus (0nis
cus asellus), the pill bug (Ar
madillidium vulgare), and Porcellio 5cab
ar); those of the order Diploda, such as Blaniulu
s guttulatus) ; Chiropoda (Chi
lopoda), such as those of Geophilus carpophagus
us) and Scutigella species (Scutig
ara 5pec, );
hyla), for example, Scutigera immaculata (Scutigera immaculata)
) ; those of spider mouths (Arachnida), such as Scorpio maurus (5scorpio maur
us) and Latrodectus mactans (Latro
dectus mactans): Ac
Arina), for example, the Acophyte mite (
Acarussiro), Argas reflexus, Ornithodoros moubat
a), red mite (Dermanyssus galli)
nae), Er1oph Jesus Libis (Er1oph
yes ribis), citrus rust mite (phyl
locoptruta oleivora), Boophilus micropulus (Boophilus m1c)
roplus), Ribicephalus everci (
Rh1picephalus6vertsi), Hyzenda = (5arcoptes 5cabiei)
, Tarsonemus 5pec,
), Clover Hada = (Bryobia prae)
tiosa), orange spider mite (Panonychu)
s citri), Panony
chus ulmi), Tetranychus tomitus (T
etranychus tumidus) and Demi/S tick (Tetranychus urticae)
): Thysanura, such as Lepisma 5acc
Harina) ; Collembola (ColleCo)
lle), such as Onychiurus armatus:
Orthoptera, e.g.
Blatta orie
ntalis), American cockroach (Peripla)
neta americana), Leucophea maderae (Leucophaea maderae),
German cockroach (Blattella german)
ica), Acheta domesticus (Acheta domesticus)
domesticus), Kellers specis (Gry
llotalpa 5psc, ), ) Locusta m igratoriamig
ratorioides), Melanoplus diffe
rentialis) and Schistocerca gregaria.
): Dermaptera
such as Horphiicula auricularis (F.
orficula auricularia);
Those of the order Termite (I 5optera), such as Reticulitis species.
ermes 5pec, ); Anopl.
ura), such as phylloxera vastatrix, Pemphigus 5p.
ec) and human lice (Pediculus
humanus corporis); members of the order Thysanoptera, such as Hercinothrips fe
moralis ) and thrips ('I'hr
ips tabaci) Heteroptera (Heteroptera)
Eurygaster species (Eurygaster 5pec), Dysdermes intermedius (Dysdercusinte)
rmedius), Piesma” quadrata (Pie
sma quadrata), bed bugs (Ci
mex 1ectularius), Rhodnius prolix, ;z, (Rhodnius prolixu
s ) and Triatoma species (Triat.
oma 5pec, ); Homoptera
ra), such as Aleurodes brassicani (
Aleurodes brassicae), cotton whitefly (Bem1sia tabaci),
) Trialeu
rodes vaporariorum), cotton aphid (Aphis gossypii), radish aphid (Breviocoryne brassic)
ae ), Cryptomys livis (Cryptomy
cus ribis), Doralis-siafly (Dor
alis fabae), Doralis pomi (Dor
alis pomi), Eriosoma lanigerum (
Eriosoma lanigerum), peach aphid (Hyalopterus arundi)
nis); wheat aphid (Macr
osiphum avenae), Mizus serrano (
Myzus cerasi), peach aphid (Myzus cerasi), green peach aphid (Myzus cerasi)
Myzus persicae), Pholodon humuli, Rhopalosiphum pad
i), :r-Empoa species (Empoa
sca 5pec, ), Eu5celis bilobatus, Nephotettix cincti
ceps), dogwood scale insect (Leca
nium coni), Laodelphax 5triatsllu, Laodelphax 5triatsllu
s), brown planthopper (Ni1aparvata)
lugens), red scale insect (Aoni
diella aurantii), white scale insect (Aspidiotus hederac)
, Pseudococcus species (P 5eudoc
occusspec, ) and Psilla species (P
syllaspec, ); Lepidoptera
ra), such as the cotton aphid (Pecti
nophoragossypiella), Bupalus piniariu
s), Keimadovia Bu/lz Mark (Chsim
atobia brumata), Lysocholetis
Plancaldera (Lithocolletis bla)
ncardella).

Hyponomuta bapula (Hyponomutap)
adella ), diamondback moth (P 1utella ma
culipennis).

Malacosoma neustria
), Euproctis chrysoloe (Euproctis
ischrysorrhhoea), Lymantria species (Lymantria 5pec, ), Futskaratrix sulberiella (Buccalatr.
ix thurb6rilla), Phyllocnistis citrella
, Agrotis species (Agrotis 5pec)
, ), Euxoa species (Euxoa 5pe
c, ), Feltia species (Feltia
Spec, )Nearly Insulana (Earia
s 1nsulana), Heliothis species (He1iothis 5pec, ), Laphygama exigua
, Armyworm (Mamestra brassicae)
), Panolis flam
mea), Prodenia 1
itura), Spodoptera species (5po
doptera 5pec, ), Trichobrusia
Trichoplusia ni, Carpocapsa pomone
lla), P 1eris
5pec, ), Chilo species (Chilo 5
pec, ), Pyrasta nubilalis (Pyra
usta nubilalis), Ephestin kjihniella
), honey hemlock (Ga1leria mellone)
lla), Cacoecia podana (Cacoecia
podana), Capua L/Chiclana (Ca
pua reticulana), Christoneura
Choristoneura fum
iferana), Crysia ampiguera (C1y
sia ambiguella), Chabamaki (Ho
mona magnanima) and Tortrix viridana
: Coleoptera, such as Anobium punc.
(Rh1z)
opertha dom 1nica), Bruchidiusobtecmes
tus), bean beetle (Acantho
scelides obtectus), Hylotrupes bajulu (Hylotrupes bajulu)
s), Agelastica a/'2
ca alni), V petinotarsa decem lineada (Lept inotarsadecem 1in.
eata), Phaedon cochleariae (Phaed
on cochleariae), diabrotica°
Species (Diabrotica 5pec,),
Psylliodes chrysosephala
chrysocephala), Epilachna varibestis
), Atomaria Species (Atomaria 5
pec , ), saw-whet beetle (0ryzaep
hilus surinamensis), Anthonomus species (Anthonomus 5pec)
), Sitophilus species (S 1top
hilus 5pec, ), Otiorrhync hussulca
tus ), the cabbage weevil (Cosmopolit
es 5ordrdus), Ceuthorrhynchus 6 assimilis (Ceuthorrhynchus assim)
ilis), Hypera °postica (Hypera po
stica), Dermestes species (Derm
estes 5pec, ), Trogoderma species (Trogoderma 5pec, ), Anthrenus species (Anthrenus 5pec)
), Attagenus species
s 5pec, ), Lycmes species (Lyc
tus 5 pec,), Meligetes Aeneus (Me
ligeth aeneus), Pt1nus 5pec, Pt1nus hololeuc, N1ptus hololeuc
us), Gibbium
psylloides), Tribolium species (Tribolium 5pec, ).

Tenebri.

molitor), Agriotes species (A
griotes 5pec, ), Conoderus species (Conoderus 5pec, ), Melolontha melo
lontha), Ampaimallussolostitialis
) and Co5tel
ytra zealandica): Hymenoptera (
Hymenoptera), such as Diprion 5pec,
Hoplocampa 0 Species
5pec, ), Lanius Species (La5
ius 5pec, ), Monom
orium pharaonis) and Vespa.

Species, Z. (Vespa 5pec,): those of the Diptera, such as Aedesspeci, 7 Anopheles specii (Anopheles 5pec)
, ) , Cu1ex 5pe
c, ), Drosophila melanogaster
hila melanogaster), house fly (
Muscadomestica), Fannia species (Fannia 5pec,), stable fly (S
tomoxycalcitrans), Hypoderma species (Hypoderma 5pec,
), B 1bio hortu
lans), Qscinela furito (Qscinel)
la frit), Formia species (Pho
rmia 5pec, ), P. r.mia (P.
egomyia kyoscyami), Caliphora erythrocephala (Caliphora eryt)
hrocephala), Lucilia species (L.
ucilia 5spec, ), ChrysOmyiaspec, Ceratitiscapitat
a), Dacus oleae
) and T 1pula pa
ludosa): as well as the Flea order (5iphona
ptera), such as those of the Chaeopus rat flea (
Xenopsylla cheapis).

The active compounds according to the invention can be used in conventional compositions, such as solutions, emulsions, wettable powders, suspensions, powders, powders, foams, liniments, wettable powders, granules, aerosols, concentrated suspensions, emulsions, Powders for seed treatment, natural and synthetic substances impregnated with active compounds,
Microscopic capsules in polymeric materials and in coating compositions for use on seeds, and compositions for use with combustion devices, such as fumigation cartridges, fumigation cans, fumigation coils, etc., and ultra-concentrated Can be converted into cold mist and warm mist compositions for low volume application.

These compositions are prepared in known manner, for example by combining the active compounds with extenders, i.e. liquid or solid or liquefied gaseous diluents or carriers, and optionally surfactants, i.e. emulsifiers and/or dispersants and/or blowing agents. It can be prepared by mixing.

When using water as an extender, for example, an organic solvent can be used as an auxiliary solvent.

Preferred liquid diluents or carriers are aromatic hydrocarbons such as xylene, toluene, benzene or alkylnaphthalenes, chlorinated aromatic or aliphatic hydrocarbons such as chlorobenzene, chlorethylene or methylene chloride, aliphatic hydrocarbons. , for example cyclohexane or paraffins such as mineral oil fractions, alcohols such as butanol or glycols and their ethers and esters, ketones such as acetone, methyl ethyl ketone,
Methyl isobutyl ketone or cyclohexanone or strong polar solvents such as dimethylformamide, dimethyl sulfoxide or acetonitrile, as well as water are used.

By liquefied gaseous diluent or carrier is meant a liquid that is a gas at ambient temperature and pressure, for example an aerosol propellant such as a halogenated hydrocarbon (eg Freon).

As solid diluent or carrier preferably ground natural ores such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorinite or diatomaceous earth, or ground synthetic ores such as highly disperse silicic acid, alumina Or use silicate.

Suitable examples of emulsifiers and blowing agents include nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, holoxyethylene fatty alcohol ethers, such as alkylaryl polyglycol ethers,
Suitable examples of dispersants include lignin sulfite waste liquor and methylcellulose.

The active compounds according to the invention can be present in compositions mixed with other active compounds.

Generally the above compositions have a
Contains ~90% by weight of active compound.

The active compounds can be used as such or in their compositions or in the application forms prepared from them.

Application can be done by conventional methods such as jet spraying, liquid spraying,
It can be carried out by spraying, powder application, granule application, fumigation application, evaporation application, liquid application, smearing or adhesive application.

The concentration of active compound in the preparations can be varied within a fairly wide range.

Generally this concentration is from o,oooi to 10% by weight, preferably from 0.01 to 1% by weight.

The active compounds can also be used with good results using the ultra concentrated low volume method (ULV), in which active compounds 9
It is also possible to use up to 5% of the composition or only 100% active compound.

When used against pests harmful to health and stored crop pests, the active compounds are characterized by good residual activity on wood and soil and good stability towards alkalis on lime-treated substrates.

Therefore, an insecticidal or acaricidal composition can be obtained by incorporating the present compound as an active ingredient in a mixture with a solid or liquefied gaseous diluent or carrier, or a liquid diluent or carrier containing a surfactant.

In addition, by applying the compound alone or a composition containing the compound of the present invention mixed as an active ingredient with a diluent or carrier to pests or their habitat, insects,
Or mites can be exterminated.

Furthermore, the compounds, alone or in mixtures with diluents or carriers, can be applied to the crop field just before and/or during the growing season to protect the crop from damage by insects or mites.

The present invention therefore improves the conventional method of providing harvested crops.

The insecticidal activity of the compounds of the present invention is illustrated by the following experimental examples.

Experimental Example A P 1tella Test Solvent: 3 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To prepare a suitable formulation of the active compound, 1 part by weight of the active compound was mixed with the above amount. The emulsifier was mixed with the above amount of solvent and the concentrate was diluted with water to the desired concentration.

Cabbage leaves (Brassicu oleracea)
) is sprayed with the active compound preparation until drippings and then the diamondback moth (P 1utella ma
culipennis) caterpillars.

The degree of mortality (%) was measured after a certain period of time.

100% means that all caterpillars are killed, and 0% means that no caterpillars are killed.

The active compound, the concentration of the active compound, the evaluation time and the results are shown in the table below.

Experimental Example B Laphygma Test Solvent: 3 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To prepare a suitable formulation of the active compound, 1 part by weight of the active compound is combined with the above amount of emulsifier. and the concentrate was diluted with water to the desired concentration.

Cotton leaves (Gossypium hirsutum)
of the active compound preparation until drippings and then the next owlet moss (Laphygmae
xigua) caterpillars were allowed to grow.

The degree of mortality (%) was measured after a certain period of time.

100% means that all caterpillars are killed, and 0% means that no caterpillars are killed.

The active compound, the concentration of the active compound, the evaluation time and the results are shown in the table below.

Experimental example C Green peach aphid (Myzus) test (contact activity)
Solvent: 3 parts by weight acetone Emulsifier: 1 part by weight alkylaryl polyglycol ether To prepare a suitable formulation of the active compound, 1 part by weight of the active compound is added to the above amount containing the above amount of emulsifier. Mix with solvent and dilute concentrate with water to desired concentration.

** Green peach aphid (Myzu)
Cabbage plants (Brassicaoleracea) that are heavily infected by Brassica oleracea
The active compound formulation was sprayed onto the solution until dripping wet.

The degree of mortality (%) was measured after a certain period of time.

100% means all aphids have been killed, and 0% means no aphids have been killed.

The active compound, the concentration of the active compound, the evaluation time and the results are shown in the table below.

Experimental Example D Tetranychus Test (Resistance) Solvent: 3 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To prepare a suitable formulation of active compound, 1 part by weight of active compound was mixed with the above amount of solvent containing the above amount of emulsifier and the concentrate was diluted with water to the desired concentration.

A beanstalk (Phaseolus vulgaris) having a height of approximately 10-30 crrL was sprayed with the active compound formulation until dripping wet.

Two-spotted spider mites (T e
trannychusurticae).

The degree of mortality (%) was measured after a certain period of time.

100% means all the two-spotted spider mites die, and 0% means none die.

The active compound, the concentration of the active compound, the evaluation time and the results are shown in the table below.

Experimental Example E LD100 Test Test Animal: 5itophilus granariu
s Solvent: 2 parts by weight of acetone of active compound were added into 100 parts by volume of solvent.

The solution thus obtained was further diluted with solvent to the desired concentration.

2,5 rnl! A solution of the active compound was pipetted into the Petri dish.

At the bottom of the Petri dish was a piece of paper with a diameter of approximately 9.5 cm.

The Petri dish was not covered until the solvent had completely evaporated.

The amount of active compound per 1rrj: of paper varied depending on the concentration of the solution of active compound.

Approximately 25 test animals were then placed in Petri dishes and covered with a glass plate.

The condition of the test animals was observed for 3 days after the start of the experiment.

The degree of mortality (%) was measured.

100% means death of all test animals, 0% means no death.

The active compounds, concentrations of active compounds, test animals and results are shown in the table below.

Experimental Example F LT1oo test for Diptera Test animal: Aedes aegypt
i) Solvent: 2 parts by weight of acetone of active compound were added in 1000 parts by volume of solvent.

The solution thus obtained was further diluted with solvent to the desired concentration.

2,5 rnl! A solution of the active compound was pipetted into the Petri dish.

At the bottom of the Petri dish is a t-shaped piece with a diameter of approximately 9.5 cm.
There was paper.

The petri dish was not covered until the solvent had completely evaporated.

The amount of active compound per m' of paper varied depending on the concentration of the active compound solution.

Approximately 25 test animals were then placed in Petri dishes and covered with a glass plate.

In the test, the condition of the driven object was continuously observed.

The time required for 100% killing was measured.

Test animals, active compound, active compound concentration and 100%
The table below shows the killing time of

Experimental Example G “T100 test for Diptera Test animal: Musca domestica
ica) Solvent: 2 parts by weight of acetone of active compound were added in 1000 parts by volume of solvent.

The solution thus obtained was further diluted with solvent to the desired concentration.

2.5 ml of the active compound solution was pipetted into the Petri dish.

At the bottom of the Petri dish was a piece of paper with a diameter** of approximately 9.5 CrIL.

The Pel-'J dish was not covered until the solvent had completely evaporated.

The amount of active compound per paper of IK varied depending on the concentration of the active compound solution.

Approximately 25 test animals were then placed in Petri dishes and covered with a glass plate.

The condition of the test animals was continuously observed.

The time required for 100% killing was measured.

Test animals, active compound, active compound concentration and 100%
The table below shows the killing time of

EXPERIMENTAL EXAMPLE H Test 1 with Parasite Larvae Solvent: 35 parts by weight of ethylene polyglycol monomethyl ether Emulsifier: 35 parts by weight of nonylphenol polyglycol ether To prepare a suitable formulation of the active compound, 30 parts by weight of the active substance of the invention were mixed with the above amount of solvent containing the above proportion of emulsifier and **the concentrate was diluted with water to the desired concentration.

Approximately 20 fly larvae (Lucilia cuprina)
) was added to a test tube containing approximately 2 crtl of horsemeat.

0.5 ml of the active compound formulation was applied to the horsemeat.

The degree of mortality (%) was measured after 24 hours. 100% means that all larvae are killed, and 0% means that no larvae are killed.

The active compounds tested, the concentrations of active compounds used and the results obtained are shown in the table below.

The method of the present invention is illustrated in the following production examples.

Production Example 1 25,69 (0,1 mol) of 1-(3-)lifluoromethylphenyl)-3-hydroxy-1,6 dihydropyridazinone (6), 20.71 (0,15 mol) of potassium carbonate, 18.8 f (0.1 mol) of 0.0-diethyl-thionophosphate diester chloride and 300 r
The mixture of fLl acetonitrile was stirred at 50°C for 4 hours.

It was then cooled to room temperature and extracted by shaking twice with 300 ml of water after addition of 400 ml of toluene.

The organic phase was separated, dried over sodium sulphate and the solvent was removed in vacuo.

The residue was separated by distillation. 33.41 (82% of theory) of 0-O-diethyl 0-CI-(3-)IJfluoromethylphenyl)-1,6-cyhydropyridazole(6)-
-(3)-ylyothionophosphate ester is 1.52
It was obtained in the form of a yellow oil with a refractive index of 40.

In the same manner, the compound of the following formula * was also prepared: 1-phenyl-3-hydroxy- required as a starting material
The 6-oxo-pyridazine derivative (e) could be prepared, for example, as follows: 171'("1 mol) of 3-trifluoromethylphenylhydrazine (for its preparation, see DE 1116534) was dissolved in a mixture of 1000 rLl of water and 250 r/l of concentrated hydrochloric acid, and then 98P ('1 mol) of maleic anhydride was added at about 90°C.

The mixture was then stirred for a further 1 hour at 95-100°C, and the crystallized product was separated after cooling the reaction mixture.

It was purified by dissolving it in dilute sodium hydroxide solution and reprecipitating with hydrochloric acid.

21 (1' (82% of theory)) of 1-(3-)IJ fluoromethylphenyl-3-hydroxy-1,6-cyhydropyridazinone (6) is a pale yellow powder with a melting point of 176°C. obtained in the form.

Claims (1)

[Scope of Claims] 1 The active ingredient is a compound of the general formula [wherein R is alkyl having 1 to 3 carbon atoms, " is alkyl having 1 to 3 carbon atoms, alkoxy having 1 to 3 carbon atoms, carbon is alkylthio having a number of 1 to 3, W and `` may be the same or different,
each is hydrogen or methyl, R is chlorine, nitro or trifluoromethyl, n is O or 1, and X is oxygen or sulfur] An insecticide and acaricide containing an acid) ester and an ester-amide.