JPS61282387A - Phosphorus-containing heterocyclic compound - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a new series of substituted ring-containing heterocyclic compounds, 1.5,2
-Oxathiaphosborinane 2-sulfide 1. s
, 2-oxathiaphosphine A 2-sulfide, several manufacturing methods thereof, and its pest control agent (p
Suitably as an arthroporcidal agent (art-comhatingαgtnt)
g), especially as insecticides (inzgcticitL)
a), for use as acaricide (acari-cida) and nematicide (rLtmaticid, g).

Certain P-heterocyclic compounds, such as 5-membered cyclic thiophosphoramide soester (nido-1°Eto), have been published in Pesticide Science Journal (7, Peyti-side Sci,
), 5.161 (197B)) or sothiophosphonic acid Ov S-diester (West German Patent Specification Letter 1.
104.520) can be used as a pest control agent.

However, the insecticidal and acaricidal action of these known compounds is not always satisfactory, especially when the active compounds are used at low concentrations and at low application rates.

General formula (I) where R represents an amine or an optionally substituted group selected from the series of alkyl, alkylamino, methylalkylamino, alkoxy, alkenyloxy and alkylthio, R1 to Rs may be the same or different and represent hydrogen or an optionally halogeno-substituted group selected from the series consisting of alkyl, alganyl, alkoxyalkyl and alkylthioalkyl, or halogeno, nitro or dialkylaminoalkyl or phenyl or pentyl, which may be substituted, and furthermore, two of the groups R1 to Ba are substituted together with one or more carbon atoms to which they are bonded A novel P heterocyclic compound has been discovered in which P represents 0 or 1 and may form a monocyclic or bicyclic group.

The new compound of the general formula +1) is α) a halodane compound of the general formula (II), in which HaL represents halogeno, preferably chlorine or bromine, especially chlorine, and R has the above meaning; R1 to RS and R are reacted with a compound having the above meanings, appropriately in the presence of an acid acceptor, optionally in the presence of a diluent, or b) with the general formula (
IT) in which R represents an optionally substituted alkyl sothioanhydride of the general formula tV) in which R1 to R1 and R have the meanings given above, and X is halogeno, preferably chlorine or bromine; In particular, it represents chlorine or
or using an alcohol representing a sulfonic acid group of the general formula (VI)05-Y(VI) (where Y represents an alkyl or aryl which may be substituted) and an appropriate diluent, and C) In the first step (same as method α) thiophosphoryl trichloride (
PSCL, )t is reacted with a compound of the general formula (m) to form a 2-chloro-1,5,2-oxathia-P-cycle of the general formula (■) in which R1 to RI and R have the above meanings. , and then, after appropriate isolation, in the second reaction step, the compound is prepared by the general formula (■)RM(■), where R has the above meaning except for alkyl, which may be substituted. , M represents hydrogen or one equivalent of an alkali metal, alkaline earth metal (e.g. sodium, potassium or calcium) ion or ammonium ion, optionally in the presence of an acid acceptor, and optionally a diluent. It can be obtained by reacting in the presence of

The novel P-heterocyclic compounds of the general formula (I) are characterized by a high activity against pests, preferably against arthropods, in particular a high degree of insecticidal and acaricidal activity and nematocidal activity. Also, synergistic mixtures with other pest control agents (sy
nergisticmixttLre).

Surprisingly, the compounds of general formula (I) according to the invention exhibit a considerably higher insecticidal and acaricidal and nematicidal action than the corresponding known compounds.

The groups given in each general formula preferably have the following meanings.

The alkyl groups in the alkylamino group and in the methyl-alkylamino group R may be straight-chain or branched and contain 1 to 8, preferably 1 to 6, especially 1 to 4 contains carbon atoms. Methyl, ethyl, leu and i-propyl may be mentioned by way of example.

The alkyl groups of the noalkylaminoalkyl groups R1 to R' may be the same or different, and may be linear or branched, preferably 1 to 6
, especially 1 to 4 carbon atoms. methyl,
Ethyl as well as roux and i-propyl may be mentioned by way of example.

In the soalkylamino groups R1 to Ba, the alkyl group linking the sialkylamino moiety preferably contains 1 to 6, especially 1 to 4 carbon atoms.

The alkyl group R, which may be substituted, may be linear or branched, and preferably has 1 to 6 groups.
In particular alkyl having 1 to 4 carbon atoms. Methyl, ethyl, ru and i which may be substituted
-propyl, roux, i- and t-butyl may be mentioned by way of example.

The optionally substituted alkoxy group R may be straight-chain or branched and is preferably alkoxy having 1 to 6, especially 1 to 4 carbon atoms. Methoxy, ethoxy, leu and t-propoxy and w-1-1 and t-butoxy may be mentioned by way of example, which may also be substituted.

The optionally substituted alkenyloxy group R may be straight-chain or branched and is preferably alkenyloxy having 2 to 6, especially 2 to 4 carbon atoms. Propenyloxy and butenyloxy, which may be substituted, may be mentioned by way of example.

The optionally substituted alkylthio group R may be straight-chain or branched and is preferably alkylthio having 1 to 6, especially 1 to 4 carbon atoms. Methylthio, ethylthio, Ru and i-propylthio, which may be substituted, -1 and t
-Butylthio may be mentioned as an example.

In the alkyl groups R1 to Ra, which may be halogen-substituted, the alkyl may be straight-chain or branched, preferably having 1 to 6 carbon atoms, especially 1 to 4 carbon atoms. represent. Methyl, ethyl, leu and t-propyl, leu, t- and tert-butyl, all of which may be substituted by halogens, preferably fluorine, chlorine or bromine, may be mentioned, chloromethyl and bromomethyl. should be particularly selected.

The alkenyl radicals R1 to RS, which may be halogen-substituted, may be straight-chain or branched and are preferably alkenyl having 2 to 6, especially 2 to 4 carbon atoms. Mention may be made by way of example of ethynyl, propen-1-yl, propen-2-yl and buten-5-yl, all of which may be substituted by halodane, preferably by fluorine, chlorine or bromine.

The alkoxyalkyl and alkylthioalkyl radicals R1 to R1, which may be substituted by halogen (preferably fluorine, chlorine or bromine), preferably contain 2 to 8, especially 2 to 6 carbon atoms. Mention may be made, by way of example, of methoxymethyl, ethoxymethyl, methylthiomethyl, methylthioethyl and ethylthiomethyl, which are non-rodane-substituted.

Two of the radicals R' to Ba, together with the carbon atom or atoms to which they are bonded, may also be bridged by a methylene or ethylene group, on which one or two alkyl groups, preferably is one or two or more, preferably one to three, forming a 5- to 7-membered cycloalkyl or cycloalkenyl ring which may be substituted by one alkyl group, especially methyl or ethyl,
In particular, it may have as many as 1i two substituents, which may be the same or different. The following may be mentioned as examples of substituents. Alkyl preferably having 1 to 4, especially 1 or 2 carbon atoms, such as methyl, ethyl, leu and t-propyl, t- and t-butyl; preferably 1 to 4, Especially 1-! alkoxy having as many as 2 carbon atoms, such as methoxy, ethoxy, rou and i-propoxy and ru, i- and tert-butoxy; alkylthio preferably having 1 to 4, especially 1 or 2 carbon atoms; For example methylthio, ethylthio, ru and t-propylthio and ru and t-butylthio; preferably 1 to 4, especially 1 or 2 carbon atoms and preferably 1 to 5
halogen atoms, especially 1 to 5 halogen atoms
noalkyl, whose halogeno atoms may be the same or different, preferably fluorine, chlorine or bromine, especially fluorine, such as trifluoromethyl; halogeno, preferably fluorine, chlorine, bromine and iodine , especially chlorine and bromine; cyano; nitro; carbamoyl; alkylcarbonyl preferably having 2 to 5 carbon atoms and alkoxycarbonyl preferably having 2 to 5 carbon atoms. Halogeno, especially chlorine and bromine, may be mentioned as preferred substituents.

The optionally substituted alkyl group Y is preferably 1
Alkyl having from 4 to 4 carbon atoms and optionally substituted by halogeno (fluorine, chlorine and/or bromine, preferably fluorine), examples of which may include methyl and trifluoromethyl.

The optionally substituted aryl radical Y is preferably phenyl, optionally substituted by alkyl having 1 to 4 carbon atoms, 4-methylphenyl may be mentioned by way of example.

Unless otherwise specified, halogens include fluorine, chlorine,
Bromine and iodine, preferably fluorine, chlorine and bromine, especially chlorine and bromine.

Preferred compounds of the general formula (I), in which R is amino, C8-C8-alkylamino, methyl-(
C1-C,-alkyl)-C8-C8-alkyl, C,-C6, which may be substituted with amino or halodane
- Represents alkenyloxy, C1-C6-alkoxy or C0-C6-alkylthio, R1 to Ba may be the same or different, and 01-C6 may be substituted with hydrogen, halogeno, NO, or halodane -alkyl, C1-C@h-alkenyl, no(01-C4-alkyl)-amino, CI-C4-alkoxy-01-C4-alkyl, C8-C4-alkylthio-○, ~C4-alkyl, benzyl or phenyl or two of the groups R1 to R1 in the formula, together with the carbon atom or carbon atoms to which they are bonded, may be substituted with methyl or ethyl, and bridged by methylene or ethylene groups. C which may be used to form a binomial group
It forms a 6-C1 cycloalkyl or cycloalkenyl ring, and R represents 0 or 1.

Particularly preferred compounds of the general formula CI) are those in which R is C8-C4-alkyl, C,,C,-alkoxy,
C1-C5-alkenyloxy% C5-C4-alkylthio, C1-C4-alkylamino or methyl-(C
, ~C4-alkyl)-amino, R1 to R1 may be the same or different and represent C,,C,-alkyl, which may be hydrogen-, nitro- or halodane-substituted, or C0~C4-
represents alkylthio-CI-C4-alkyl, or two of the radicals R1 to R1 together with the carbon atom or atoms to which they are bonded are bridged by a methylene or ethylene group to form a bicyclic radical. It may form a 5- or 6-membered cycloalkyl or cycloalkylene ring, and n represents 0 or 1.

Particularly very preferred compounds of general formula (I) are those in which R is C, -C4-alkyl, C, -C, -C groupy,
01-C4-alkylamino or methyl-(C3-C
2-alkyl)-amino, R1 to Rs may be the same or different and represent hydrogen, or C7-C4-alkyl which may be substituted with chlorine or bromine, and R is 0 or It is something that represents 1.

Compounds of the general formula (E) which are selected as particularly preferred are those in which R represents methyl, ethyl, methylamine, trimethylamino or methoxy, and R1 to Rs may be the same or different; It represents hydrogen, methyl, ethyl or ru or t-propyl, such that ru represents 0 or 1.

The compounds of formula (I) have one or more asymmetric centers and can therefore be produced as each soastereomer individually or in the form of a soastereomer mixture.

The compound of general formula (■) is a new substance. This compound and the method for its preparation described above form part of the present invention. The preferred meaning of the definition of groups R1 to R1 is the general formula (I)
Corresponds to the preferred meaning mentioned above.

For example, if methanethiophosphonic acid dichloride and 5-hydroxy-gropyl mercabutane are used as starting materials for process embodiment (α), the reaction of these compounds can be represented by the following formula.

If ethanethiophosphonic acid soteoanhydride and 4-chlorobutan-1.-ol are used as starting materials in process embodiment (h), the reaction of these compounds can be represented by the following formula.

If thiophosphoryl trichloride, 6-hydroxyprosylmercabutane and sodium methylate are used as starting materials for process embodiment (C), the two-step reaction of these compounds can be represented by the following equation.

General formulas in), (m), (IV) required as starting materials
, (V), (Vl) and (■) are well-known compounds in organic chemistry, and can be produced using known methods and methods.

The compound of formula (■) required as a starting material is a new substance. Its preparation is carried out as described in process embodiment (C) (see also Preparation Examples).

The following compounds can be cited as examples of general formula (■).

CH8CM, H CH, C, H, H CH, rL-C, H7H CH31-CH8 3-cho C, II! I C, H, H C, E, Lou CM HC1H1
l 1-CH8 3-piece lou C1l 1-CHH 313-piece HHCH.

HE CH.

HHCH.

HHCH.

HHC,H.

HHC1Hs II HC1H.

HHC,H.

HHC,H.

CHHCH.

HHH HHH HHH HHH HHH HHH HHH HHH CM, HH CtH,HH C, H7HH i-CIl HH 3 guns C, H, HH C8H2HH i -CHHH 3F C, H7HH i-CHH11 3 guns CH8HH CH, HCH.

CHl　　　　HCH3 CH3HCH.

CH3HC,H.

CH8HCtE.

CH, II C, HICH8HC3H
.

CH8HC,H.

CIl, CH2OH.

CH, CH2OHs CH, CH, CH.

CH3CH8CIl.

C1l, Cll, C, H.

CH, CH8C, H.

CH8CH,C,H.

CH3CH, C3H.

CHl CH8C8H.

CH8CH8CE.

CH8CH8CH.

C1l, C1l, CE.

C, H, HH C3H9HH i-CHHH 3? C, H5HH C, H, HII i-CM　　　　H11 3 guns C8H,HH i-CHH8 3 guns CH,HII C, H5n　　　　H C, H, HH i-CHH8 3 guns C, H, HII C, H7HH i-CHII HC, H7HH i-CHH8 3 guns CH2OE, II CH, C, H, H Cl1. C, H7H CH, CH, CH.

E　　　　　　　　HH HHH HB　　　　　　　H HHH H to CH3H.

HII CH.

HHCM.

HII CH.

H.H.C.E.

CH, i-CM　　　H 3? HCH3CH.

HC'H, C, H.

H0M3 C, H.

HCH,i-C,H.

CH, CH, CH.

CH3CH,H CH,C,,H,H CH,C,H,H CH,1-CHH 3-CM, CH,HH CH,C,H,HH CH3-CHHH 3FCH,1-CHHH C,U5 C,H5E HC,H
, Lou CHHH Ti-("HHH C,H,,.

Lou CHi・-CHHH 373 cho HHCH8CH.

HHCH8C,H.

HHCH,C,H7 HHCM, 1-C3H.

B　　　　　HC2H,C,H.

HHC, E, C3H.

HHC', H, i　-C,H.

HHC, 11, C, H.

H, HC, II, i-C8H.

HCH, CII.

CM.

CH, HCH, C, H,.

HHHH HHHH HHHH HHHH HHHH HHHH HHHH HHHH HHHII HHHH HIj 　　　　HH HHHH HHHH HHHH HHHH HHHjl HHHB HHB　　　　　H HHHH CH, HCH3C, H.

CH, M　　　　　　CH,i　-C5H.

CB5　　　　E　　　　　　C, H, C, H.

CH8If C,H,C,H7CH8E
C,H,i -CH3teCH,HC,H,C2H3 OM3 HC,II, 龜-CHC
H, CH3CH, CH3 CH3CH, CH3C, H.

CH3CH,CM, CH3CH3CM,
CH3i-C8H.

CM, C1l, C, H, C,
H.

CH3CH, C, H, C8H.

CH, CH3C2Ml1 i-C,H.

CH, CH8C8H, C3H.

CH3CH, C'3H7i -C2H3OMs,
CH, C113CH3OK, CB,
CB5 CH3CH3CH3CH,
CH3 HHHH HHHH B HHII HHHH HHHH HHHH HHHH HHHH HHHH HHHH E HHII HHHE HHHH HHHH HHHH HHHH CM, HHH CHHH11! 5 C3H, HHII CH8CH, CM, CH.

if HHH if ff HHfl
gHHfl
HHH CH, HCM, CH.

HHHH HHHH ff g 11
HHHHH Hg HH Hg HH if HHH HHHH HHII CH3 ff ff HCH.

H11HCH.

HHHCH3 1-CHHH sfu CH,CH3HH CH, C, H, HH CH3C,H,H11 CHs　　　　　　-CHHH 3? CH8CM, HH HHCH8CHl HHCH,C,H.

HHCM　　　　　　C,H.

HH (1’Ms L-CHH.

HHC1l, H HHC,H,H HHC1H, H g g i-c8g,
nCH, HCM, H CH, HC, H, H CH, HC3H7H CH, Hi-CM, H s Substantially the inert organic solvent for process embodiments a), h) and C) according to the invention. , and as a solvent for the preparation of new compounds of general formula (■). This includes, in particular, aliphatic and aromatic, optionally halodanated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, pensone, ligroin,
Benzene, toluene, xylene, methylene, ethylene, chloroform, tetracarbon L, chlorobenzene and O-dichlorobenzene; ethers, such as soether and diptyl ether, glycol methyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane Ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone and methyl isobutyl ketone; Esters, such as methyl acetate and ethyl acetate; Nitriles, such as acetonitrile and probionitrile; Amides, such as trimethylformamide, trimethylacetamide and N-methylgyrolidone; and dimethyl sulfoxide, tetramethylene sulfone and hexamethyl phosphoric triamide.

Process embodiments α), h) and C) according to the invention (general formula (
(2) (including the method for producing the compound) is carried out on general yarn at a temperature of 150°C to 120°C, preferably in the range of 0°C to 110°C. These reactions are generally conducted under atmospheric pressure.

The method embodiments α), b) and C) (including the method for producing the novel compound of general formula (■)) are suitably carried out in the presence of an acid acceptor. All conventional acid binders can be used as acid acceptors. Alkali metal carbonates and alcoholades, such as sodium and potassium carbonate, sodium methylate, potassium ethylate, sodium ethylate, and potassium ethylate, and aliphatic, aromatic and heterocyclic amines, such as triethylamine, trimethylamine, trimethylaniline. , damethylbenzylamine and pyridino are particularly useful.

Since no acid is produced when carrying out each of the method embodiments described in this invention, the addition of an acid acceptor is not necessary.

To carry out process embodiment α) according to the invention, (so)thiophosphoric acid dichloride or (di)thiophosphonic acid dichloride (
Preference is given to using 1 to 1.6 mol, in particular 1 to 1.4 mol, of a compound of general formula (m) per 16 liters of formula (n)).

To carry out method embodiment b) according to the invention, the formula (TV)
Preference is given to using from 2 to 52 mol, in particular from 2 to 2.8 mol, of the compound of general formula (V) per mole of ditheophosphonic anhydride.

To carry out process embodiment h) according to the invention and also for the preparation of compounds of general formula (■), thiophosphoryl trichloride 1
Preference is given to using from 1 to 1.6 mol, in particular from 1 to 1.4 mol, of a compound of the general formula tm) per mole, and
1 to 1.6 mol per mol of the compound of general formula (■),
Preferably, a compound of general formula (■) having 1 to 1.4 cells is used. When R represents amine, alkylamino or methyl-alkylamino and M represents hydrogen, preferably 2 to 52 per mole of the compound of general formula (■);
In particular, 2 to 2.8 mol of the compound of general formula (■) is used.

Work-up can be carried out by conventional methods, for example, extraction of the product from the water-diluted reaction mixture with toluene or methylene chloride, washing of the organic phase with water, drying and distillation or so-called first distillation ( inzipignt rL
iztiLLation)', i.e. by gentle warming for a long time under reduced pressure or by chromatographic purification on a silica dal, in order to completely remove volatile components. The subject compound is characterized by its refractive index, melting point, Rf value or boiling point, or "P-NM
Identification is based on the chemical shift of R.

In agriculture, the active compounds are well tolerated by plants and their toxicity to warm-blooded animals remains at a favorable level.
In forestry, in the protection of stored products and raw materials,
In addition, in the field of hygiene, harmful animals (
(animal pgzt), preferably for controlling arthropods, especially insects, arachnids and nematodes. The active compounds are active both against normally susceptible and against normally resistant species and against all or several stages of growth.

The above-mentioned pests include: those of the isopod (JzoporLα), such as Oniscus, Acellus ('OrLizcwz αzgZZtI),
Okadango Jh'/(ArmarLdiLLitium
vttL-1αrs), and polycellulose cover (Porcg-1Lio zcahar): those of Diplopoda (DipLoporLα), such as Planiurus gutlatus (Bl, arLiwLμsgu).
ttwLatuz) ; those of the order Chiloporidae, e.g.
Gaophilut
carpophagus) and Scut
i-ggrcL zpp, ): those of the order Symphyla, such as ScutigarsLL
aimmacuLata )H Thysanwra, e.g. L/7'
Sea r-Sara-) Y Lina (Lapizma zacc)
hatrina) Collembola (CoLlarILho)
la), such as Oni + Ursu almas (O
nychiμfW,? armatuz)? Orthoptera, such as Blatta orientalis.
taLiz), American cockroach (ParipLana)
taαmmricanα), Leucophae materae (
LgwcopnagarnacLaraa,-),
Chabane d'Equipri (BLattgLla ggrm
anica ), Acha domestic x (Acha
tar Lomgz-ticuz), mole cricket (GryL)
LotaLptt JFFF, ), Tonosara locust (
Locustα migratoriamigrato
rioidgz), melanop/l/s, diphelenchialiy, (MgLanopltuz difftra
n-tiaLiz) and Schiztoagrca grayaria (Schiztoagrca grayaria)
: Those of the order Dgramaptgra, such as Forficula auricularia (Forfi-c
uLa auric*bLaria): H: Those of the order Termite (Izoptgraα), such as RεtityuLitmrmmz zp
p, ); members of the order Anoplurα, such as PhyLoxera bastarix (PhyLloxgrαv);
aztatrix), Pgmphi
guyzpp, ), human lice (PgrLictLLt
bz hwrnα-nut corporate)
? Hagma-topinμzzpp,
) and the hair louse (Lirbegrsαthuz
JFFF, ): MaLLophaga
)O things, such as Tricot L.
gctaz #PF, ) and Gumalinea (DarlL
aLi3ga JFFF,): Thripsipidae (Thy
zαle apterα), for example, Clybane Abmilla? (HgrcinothripzfamoraLiz
) and Negiabmir-r (Thripztabac
i)? Hemiptera (Hatgroptera), such as the chai oi sting beetle (1':urygazttr JFPF)
, ), Dyzderus Intermezuus (DyzcL
ar-cuz intermmcLiuz), Pjazma qu, adrat
a), bedbug (C1mg5: Lgcttt
Lariuz), Rhodnius prolix (Rhot
iniuz proLixtbz) and triad-
r (Triatorna JFFP,): Homoptera (
Homoptar α), such as Alturodap hrazzi-ca
g), cotton whitefly (BgnsizieL tah)
aci), Trialeudes, Barrariorum (Tria
Lau-rotLaz vaporariortbm
), cotton aphid (Aphis gozzypi)
i), Japanese radish ab 2mu'y (Braviocor
yna hrazzicag), Cryptomydus
Cryptomyzuzribiz, Doralizfabaa, Doraliz-yt? DoraLizpomi, apple boll beetle (Eriozomabans srμm), peach aphid (Hyα-Loptaruz ar
trLtiniz), wheat aphid (Ph.
orotLots humuLi), wheat aphid (RhopaLoziphwm patLi)
), Empoatca ppp, )
, Nice Scelis Jar Bilobass (Euzcaliz
hiLoba-twz), black leafhopper (Na
photomttixcincticapz), dogwood cinctica 2 insects (LgctoLnium corn
i) , , 1-Leap Katakai tf') Mushi (Sa
izzgtia oLaag), Japanese brown planthopper (
LaodgLpanax ztrialLuz)
, brown planthopper (Nilaparυαta ZtL)
yg3#), Akamarukai is Ram7 (Aotsidia
LLααtLrαntii), Shiromarukai is 2 insects (
AzpirLiotuz hgdtrag), Deshudococctca, x, (Pzgudococctbz
#PF, ) and Kinorami (PzyLLa JFPP,
)? Lepidoptera (Lgpidoptara) such as cotton aphid (Pgcti3ophophorag)
ozzypigLLα), Pnogulus vinialius (
Bupa Lwr piniariuz), Chgimatohia 17T Ru ruri (Chgimatohia h
rumata), Lithochole, Chis plancaldera (
Lith@co-1Latiz hlancardg
lLa), Hyponomyutalisedera
guta pacLiLLa), diamondback moth (PLtbt
gltLa macwLipgnrbiz), MaLacoztoma nguztria
), Euproctiz ch.
ryzo-rrhoga), gypsy moth (Lyrna
ts-triazpp, ), BuceuLatriz thurbgri
glLa), Citrus leafminer (PhyLocrb)
iztiz citrg-ZLa), Yaga (Agro
tiz zpp, ), Euxoa J
PPF, ), FgLtia JFFF,
), Nearaz 1nz
Wl, ana), ttis (HaLieti)
z zpp, ), Laphyy
ma gxi gua ), armyworm (Marna
ztra brzzicaa), Panoris flammia (ParLoLiz flamrnaα), Spodoptera litvLra
), Spodoptgra zpp,
), TrichopLuzia
ni), Carpocagusa pomonella (Carpoc
apza pomongLLa), 7 snails (Pig
riz,? 7)F, ), Chil
o zpp. ), Awanomei (pyταμ−eta
nuhiLaLiz), Susokonamadaramaiga (
Ephaztia ktbghnigLla), /%
Demitsu (GaLLgria mmLLotsgll
a), TinaoLa
bitzaLlrigLLa), Tinaa perionella (Tinaa pgLLio3alLa), Hofmanophila bush-tospletella (Hofn%a3no
phiLa pzglLcLozprgtgLLa
), power = +z Cacoacia pot
Lana), Cub 7-t, 'Chiclana (CaplLa
τ-ticwLana), Corizto-naura fbmi
j'aratsa), Crisia Ambiguera (CL
yziα α諷biyuaLLα), Chaba Maki (HO
Groove α may be corner α), l”) root.

Tortrix viricLa
rLa); of the order Coleoptera (CoLaoptara);
For example, Anobium punctatum (Aru ohiurn)
Rhi-zopartha dominic, a
), Purcinous Ju optectus βs (BrtLchit
Liwz ohtacttbz).

Indan bean weevil (ACα ruthozcaLitL)
azohtact cram school
HyLotrwpaz bajwLwz), AgaLaztica alni
), Rhesotinotarsa decemlineata (Lgptirb
otα-rza tLacarnLingata)
, Phaedon-cochleariae (PnαadOle co
chLaariaa), Soaprotica (Diabro
tica JFFF, ), Pzyliodes chrysocephala (PzyLliotgzchryzocgpn La
), EpiLac13a
varivgztis), 7 Tomaria (Atomar)
ia spp,), Sawtooth beetle (□yyzα
-Ple 1LvLz ztbrinαmarbziz
), flower weevil (Af & thonomuz zpp
, ), Black weevil (SitophiLμJF#7) 7
), )% Oteorrhynx sulcarus (Otiorrh)
ynt-bowμIzwLcatbz), Chzmo-poLitaz zordiduz
), Chute Lynx easimilis (Cguthorr)
hyrbchusatzimiLiz), Eyparapoeticα, Dtrrngttazzpp, Toroidal-r
(TryogocLarmazpp,), Anthrgnuz spp, 7ri'l'5
Attagmnwz, ?FP,), Lyctμzzpp, Lyctμzzpp, MaLiggthaz α-yLguz!
, Pti3v & z zpp, Niptuz koLoLa
wcμ#), Gibhiurn
pzy-LLoidat), Kokunsutomodoki (
Tribo-Lium JFF-), f Tanabrio monito
r), click beetle (Agriotaz JFPF)
,),=+/Denis(Co3o-cLarvLs z
pp, ), MgLoLon
tha maLeLonthα), Amhuimaron・
Amphimal Lo3soLs
titiαLie) and CoztalytrcL zgaLarbd, ica
); HymarLoptara;
For example, the pine sawfly (Diprioh JFF),
HopLocetrnpa JFFF
, ), oxus (Lttziwzzpp), house ant (Ma3omOriumphalaniz) and wasp (Vgzpazpp.); those of the order Diptera (Diptgrα), such as Aedes (,4
gdgJP zpp,), Anopheles mosquito (Aruophg1
gzzpp,), Ieriki (ClLLgx JFF,),
Drosophila melanogaster x
gLano-gaztar), Yeba x (Ml&z
ca zpp, ), Himei fly (Fanr&ia
zpp, ), Black fly Erychlocephala (Ca
LLiphoro gry-throcgphaLα
), LuciLiαzpp, ), Chryzomyiazpp x (Chryzomyiazpp, ), Cuterepla (
Cutgrgbra zpp,), (Stomoxy
z JFPF, ), Ogzt-ruz
zpp, ), cow fly (Hy71) ador77! α
zpp, ), Abu (TabarLuz zpp,
), Tania (Tann1a, ?FF,), Bibi.

hartTLlanuz), Oscinera Kushi Frito (
OtcirLtlLa frit), Ptgomyia ypp, Ptgomyia yozcytmi, Cgratitiz c.
apitata), fruit fly Aeolea x (Daawz
olsaag) and ttenbo ψnoya rudosa j
TipμLα PαLμcLoza); Chiliformes (, 5i
phonaptmra), such as XgnopzyLLtx clumi o-piz
) and Suga Nomi (CgratopyLltLzIPp
); those of Arachnir (Arachnir La), such as Scorpio mauru
t ) and Latrodectus mactans (J:, atr
tycLac-twz mrLctanz): Members of the order Acari (ActLrinα), such as Acaruz tire and Acaruz tire.
rgaz,? F7), ), Kazuki Dani (0r3it
ho-rLoroz zpp, ), red mites (Darr
natsyzzzz1αl, Linat), Er1ophyez rihiz
), citrus rust JI'2 (phyLLocoptrut
aoLaivora), Oushima/2 (Baoph
iltLz zpp,), Koitamada = (Rh1p
i-caphalwz zpp,), Amblyot (AmblyOmma JFPF,), Ibo-tani (HyaLomma zpp,), ? tick
(IxotLgzppp-), Kyusenhizenda =
(Pzoroptaz!PP,), Choritptazzzpp,), Hisenda = (5
arcoptaz zpp, ), dust mites (Tar
zo3mmuz JFFF, ), cloverf = (
Bryobia pragtioza), Citrus apple cod = (Pttnyc le we ppp,)
and two-spotted spider mite (Tatranychuy JFFF)
,).

Plant parasitic nematodes include: Pratylatschup zpp,
Radopholus zi
rni-ti#) [Namikukisey f Yuu (Dity
LgrLehzd, 1ptaci), Citrus nematode (TyLarb-1?Af&Zl&#ztSi)
panatranz ), cyst nematode (Hatt
rodgra zpp, ), Nekopusu nematode (Me
loitogynt zpp, ), Aphelencoides (Aphelincoides zpp,), Longido A/su [Lonyidorsbz zpp,)
, Kusifine? (Xiphintma JFF
F, ) and Trichod A/su (Trichod, oruz
ppp,).

The active compounds can be prepared in conventional formulations, e.g. solutions, emulsions,
suspension, powder, foam, yeast, granules, aerosol,
Natural and synthetic materials impregnated with active compounds 1 Microcapsules in polymeric substances and in seed coating formulations, as well as formulations for use with combustion devices, such as fumigation cartridges, fumigation cans, fumigation coils, etc. Furthermore, it can be converted into ULV cold mist and warm mist formulations.

These formulations are prepared in a known manner, for example by combining the active compounds with extenders, i.e. liquid solvents, pressurized liquefied gases and/or solid substances, optionally with surfactants, i.e. emulsifiers and/or dispersants and /or obtained by mixing using a foaming agent. If water is not used as the bulking agent, organic solvents, for example, can also be used as auxiliary solvents.

Principal suitable liquid solvents include: aromatic hydrocarbons such as xylene, toluene or alkylnaphthalenes; chlorine-substituted aromatic or chlorine-substituted aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride; cyclohexane or nografins. aliphatic hydrocarbons 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; highly polar solvents such as trimethylformamide and There is dimethyl sulfoxide as well as water.

By liquefied gas extender or carrier is meant a liquid that is a gas at normal temperature and pressure, such as aerosol propellants such as halodane-substituted hydrocarbons, as well as butane, gas, nitrogen, and carbon dioxide.

Suitable solid carriers K are: for example, kaolin,
Crushed products of natural minerals such as clay, talc, chalk, quartz, atanogusoyite, montmorillonite or diatomaceous earth,
and synthetic mineral grinds such as highly dispersed silicic acid, alumina and silicates.

Suitable solid carriers for the granules include: crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic coarse powders; organic materials, e.g. sawdust,
There are granules of coconut husks, corn cobs and tobacco stalks.

Suitable emulsifiers and/or foaming agents include: for example polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers such as alkylaryl glycol ethers, alkyl sulfonates, alkyl sulfates, arylsulfones. There are nonionic and anionic emulsifiers such as acid salts and albumin hydrolysis products.

Suitable dispersants include Nikutobari Danine-sulfite waste and methylcellulose.

Adhesives such as carboxymethyl cellulose and natural and synthetic polymers in powdered, granular or latex form, such as gum arabic, polyvinyl alcohol, and vinyl acetate, and natural phospholipids such as kefpurin and lecithin, and synthetic phospholipids are also present in the formulation. It can be used for

Other possible additives are mineral and vegetable oils.

Inorganic pigments such as iron oxide, titanium oxide and Prussian blue, and organic dyes such as alizoline dyes, azo dyes and metal phthalocyanine dyes, as well as trace amounts of nutrients such as iron, manganese, boron, steel, cobalt. , molybdenum and zinc salts can also be used.

The formulations generally contain from 0.1 to 95% by weight of active compound, preferably from 0.5 to 90% by weight.

The active compounds according to the invention may be used in combination with other active compounds, such as insecticides, baits, sterilizers, acaricides, nematicides, in their commercial formulations and in the use forms prepared from them. It may be present as a mixture with agents, fungicides, growth regulators or herbicides. Pesticides include, for example, phosphate esters, carbamates, carboxylic esters, chlorinated hydrocarbons, raw phenyl carbon, and substances produced by microorganisms.

The active compounds according to the invention can furthermore be present in mixtures with synergistic agents in their commercial formulations and in the use forms prepared from them. A synergist is a compound that increases the action of the active compound; the added synergist need not itself be active.

The active compound content of the use forms prepared from commercially available formulations can vary within wide limits. The active compound concentration in the use forms can be from 0.0000001 to 95% by weight, preferably from 0.0001 to 1% by weight.

The compounds are used in a conventional manner appropriate to the mode of use.

When used against sanitary pests and stored product pests, the active compounds are distinguished by an excellent residual action on wood and clay and good stability against alkalis on lime-treated substrates.

The active compounds according to the invention are also suitable in the field of animal breeding and animal husbandry for the control of undesirable pests, such as insects, ticks and other acarids, by controlling harmful formations. , good results such as increased milk production, weight gain, improved quality of animal hide,
Long life etc. are achieved.

In these fields, the active compounds according to the invention are used in known manner, such as for external application in the form of dipping, spraying and pouring, and topical application.

The following examples are intended to explain in more detail the preparation of the materials according to the invention.

Example 1 First, 16.5 g of ethanethiophosphonic acid dichloride (α
1 mol) in 1 NO of toluene was introduced, and 10
A mixture of 11 g (α1 mol) of mercagtopta/-1-ol in 0 m/m of tetrahydrofuran and 22.9 (0.22 mol) of IJ ethylamine was heated at 20°C.
Add slowly drop by drop.

The mixture is heated to 80 DEG C. for 2 days, and then 200 d of toluene and 2 ml of water are added to the reaction mixture. The organic phase is separated, washed with water and dried, and the solvent is distilled off, first under a water jet vacuum and then under high vacuum. 3”;
2-ethyl-1,5, with a refractive index of =1.5761
2-oxathiaphospheno9one 2-sulfide 11.5
．． 9 (theoretical 1?059%) is obtained.

Example 2 Ethanethiophosphonic acid dideolf, hydrate 6.21110
．． 025 mol) was suspended in 50- toluene, 5-
Chloro-2,2-','Methyl propatool 6.1.9
A solution of (0.05 mol) dissolved in 20% toluene was added dropwise at 50°C. The mixture was stirred at 20° C. for 2 hours, and then the reaction mixture was added with 5% triethylamine.
．． 6.9 (0,055 mol) is added dropwise. Then,
The mixture was heated under reflux for 2 days, cooled and then heated for 2 days.
20° of N sodium hydroxide solution are added, the organic phase is washed with water until neutral, dried and the solvent is distilled off, first under a water jet vacuum and then under high vacuum. Melting point 77~
2-ethyl-5,5-tmethyl-1°5.2- at 79°C
Oxathiaphosphoritin 2-sulfide 5.511<50% of theory) is obtained.

Example 3 Thiophosphoryl trichloride 17.9' (0.1 mol) was added to 11
A solution of triethylamine (24 g + 0.24 mol) and 3-mercagtoglopanol (9.311 (L 1 mol)) dissolved in 200-g of tetrahydrofuran was first introduced at 0°C. Add dropwise over time.Heat the mixture to 20°C and at this temperature
Stir day and night. The reaction mixture is then extracted with ice water, the organic phase is dried and the solvent is distilled off under a water jet vacuum. The crude product is further purified by filtration over approximately 500 l of silica dal using 3 l of a fluid phase (cyclohexane:acetone (parts by volume) = 1 o : i). After distilling off the solvent, 4.2 fI of 2-chloro-1,5,2-oxathiaphosphorinane 2-sulfide is obtained with a refractive index of 3 = 1.61 y s.

This chloride (58II) (0.02 mol) was dissolved in 50% tetrahydrofuran, and sodium methane)1.
Dissolve 1.9 in 50 methanol and add the 9 solution at 0 to 10°C. The mixture was stirred for 10 minutes, the solvent was distilled off under a water jet vacuum, and the mixture was washed with methylene and a saturated solution of potassium. , dried on 500 g of silica dal (CH,C
Treat with Lt solution 51).

After distilling off the solvent, 2.6 g of 2-methoxy-1,5,2-oxathiaphosphorinane 2-sulfide having a refractive index of 37=1.5744 are obtained.

The following compounds are obtained in the same manner as in Examples 1 to 3.

The following examples are intended to illustrate the biological activity of novel compounds of the general formula. In some tests a compound of the formula disclosed in West German Patent Specification No. 1.104,520 was used.

Example A LTl. . Test animal: Leucophea machi 2nd (L-μC0-P
No. of animals tested: 5 Solvent: acetone 2 parts by weight of active compound are dissolved in 1000 parts by volume of solvent. The solution thus obtained is further diluted with a solvent to the desired concentration.

Take 2.5 cm of this active compound solution in a gougette, and place a furnace test tube approximately 9.5 cIL in diameter in the bottom of the beet dish. The petri dish is left uncovered until the solvent has completely evaporated. The amount of active compound per 1-7 m'' of F paper varies depending on the concentration of the active compound solution used.

Then, place the above number of test animals in the Petri dish and cover the Petri dish with a glass lid.

The condition of the test animals is examined 5 days after the start of the experiment and the % mortality rate is determined. 100% means that all test animals died; 0% means that no test animals died.

In this test, for example, the compounds from Preparation Examples 1.2 and 3 showed 100% killing at an active compound concentration of 0.2%.

Example B Limit concentration test/soil insect test Insect: Phorbia arLt.
igua) larvae (in soil) Solvent: 5 parts by weight acetone Emulsifier: 1 part by weight alkylaryl polyglycol ether To make a suitable formulation of the active compound, 1 part by weight of the active compound is mixed with the above amount of solvent. Mix, add the above amount of emulsifier and dilute the concentrate with water to the desired concentration.

This active compound formulation is intimately mixed with the soil.

The concentration of active compound in the formulation is of no practical importance; P
Only the weight of active compound per unit volume of soil, given by Pm I=nl/l), is decisive. Fill a pot with this soil and leave the pot at room temperature.

After 24 hours, the test insects are introduced into the treated soil and after a further 2 to 7 days, the dead and live test insects are counted to determine the % effectiveness of the active compound. Efficacy is 100% if all the test insects are dead, and 0% if exactly the same number of test insects are still alive as in the untreated control.

In this test, for example, production example 1.2.5.4.6.
7.8.9.11.12.15 and 17 are
It showed 100% killing at an active compound concentration of 20 ppm, whereas Comparative Example Compound (A) did not give killing (0%) at the same concentration.

Example C Limit Concentration Test/Soil Insect Test Insect: Diaprotheca balteata (Diαbro
-tica baltaata ) <7) young = w <
* tiv) Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl iriglycol ether To make a suitable formulation of the active compound, 1 part by weight of the active compound is mixed with the above amount of solvent; The above emulsifier is added and the concentrate is diluted with water to the desired concentration.

This active compound formulation is intimately mixed with the soil.

The concentration of active compound in the formulation is of no practical importance; p
Only the weight of active compound per unit volume of soil is decisive, given by p = wlI/l).

Fill a pot with this soil and leave the pot at room temperature.

After 24 hours, the test insects are introduced into the treated soil and after a further 2 to 7 days, the dead and live test insects are counted to determine the % effectiveness of the active compound. Efficacy is 100% if all the test insects are dead, and 0% if exactly the same number of test insects are still alive as in the untreated control.

In this test, for example, Manufacturing Practice Section 1.2.5.4.6.
7.8.9.11.12.15 and 17 are
It showed 100% killing at an active compound concentration of 20 ppm, whereas the comparative compound (,4) gave no killing (0%) at the same concentration.

Example D LT. . Test/Diptera test animal: House fly (Musca domestica (HtLIk)
Number of test animals: 25 Solvent: acetone 2 parts by weight of active compound are dissolved in 1000 parts by volume of solvent. The solution thus obtained is further diluted with a solvent to the desired low concentration.

Take 2.5-liters of this active compound and place it in a Petri dish. At the bottom of this Petri dish was a piece of F paper with a diameter of about 9.5 degrees. b) Leave the IJ dish uncovered until the solvent has completely evaporated. The amount of active compound per 1 sheet of paper varies depending on the concentration of the active compound solution used. Then, the above number of test animals were placed in this test dish,
Place a glass lid on the vetri dish.

The condition of the test animals is continuously checked to determine the time required for 100% killing effect (LT, 0°).

In this test, for example at an active compound concentration of 0.002%, Preparation Example 1.3.4.6.9.11.14.
LT within 360 minutes using compounds 15 and 16.
Io. On the other hand, in the case of the comparative substance (4), LT! was achieved after 560 minutes at the same concentration. . . was not achieved (0%).

Example E Testing on Resistant Larvae of LtbciLia cwprina Solvent: 55 parts by weight of ethylene glycol monomethyl ether 35 parts by weight of nonylphenol polyglycol ether To make a suitable formulation of the active compound, 5 parts by weight of The active compound is mixed with 7 parts by weight of the above mixture and the concentrate thus obtained is diluted with water to the respective desired concentration.

Approximately 20 resistant larvae of the golden fly are introduced into test tubes containing approximately 1 cfrI5 of horsemeat and 0.5 tnt of active compound formulation. After 24 hours, the mortality rate is determined.

In this test, for example, the compounds of Preparation Examples 1.4.11.15 and 17 showed a kill rate of 100% at an active compound concentration of 30 appm.

Example F LT. . Test Test animal: Sitophulus granulius (Sito-ph
wLμ, t granαriwz ) Number of test animals: 2
5 Solvent: 2 parts by weight of acetone of active compound are dissolved in 1000 parts by volume of solvent. The solution thus obtained is further diluted with a solvent to the desired concentration.

Pipette 2.5-liters of this active compound solution into a Petri dish. The bottom of this R) 17 plate has a diameter of approximately 9.5c.
WL p paper is in the case. The vetri dish is left uncovered until the solvent has completely evaporated. The amount of active compound per 1 sheet of paper varies depending on the concentration of the active compound solution used. Then, the above number of test animals are placed in this Petri dish with a plastic lid.

The condition of the test animals is checked 5 days after the start of the study and the % mortality is determined. 100% means that all test animals died; 0% means that no test animals died.

In this test, for example, the compounds of Preparation Examples 4.14.15 and 16 showed 100% killing at a concentration of 0.02, whereas Comparative Example Compound (A) showed 60% killing at the same concentration.
It was nothing more than death.

Example G Laphygma test solvent Near part by weight of acetone emulsifier: 1 part by weight of alkylaryl polyglycol ether To make a suitable formulation of the active compound, 1 part by weight of the active compound is added to the above amount. of solvent and the above amount of emulsifier,
This concentrate is diluted with water to the desired concentration.

Cabbage (Brassica oleracea (Brαpsi (21)
The leaves of owlet mot
h(Lttphygma frwgiperd, a
)) larvae while the leaves are still moist.

After a certain period of time, the % mortality is determined. 100% means that all larvae were killed; 0% means that no larvae were killed.

In this test, for example, production example 1.3.4.7.11
．． Compounds 12.14 and 15 showed 100% killing at an active compound concentration of 0.01%, whereas comparative compound (A) showed no killing (0%) at the same concentration.

EXAMPLE H Doralis Test (Intrastem Action) To make a suitable formulation of 1 part by weight of acetone emulsifier: 1 part by weight of alkylaryl polyglycol ether active compound, 1 part by weight of active compound is added to the above amount. Mix with the solvent and the above amount of emulsion and dilute the concentrate with water to the desired concentration.

Vicia faba (Vicia fahα) seedlings that were heavily infested with the bean aphid (DoraLiz fabag) were treated with 20 μl of the active compound formulation at the desired concentration into the soil without wetting the shoots. Spray in a penetrating manner. The active compound is absorbed by the roots and reaches the buds.

After a certain period of time, the % mortality is determined. 100% means that all aphids were killed; 0% means that no aphids were killed.

In this test, for example, the compounds of Preparation Examples 3.11, 12 and 17 were tested at 1% at an active compound concentration of 0.01%.
On the other hand, Comparative Compound (A) showed no killing at the same concentration (0%).

Example J Limit Concentration Test/Rhizome Action Test Insect: Phaedon cochleariae Solvent: 5 parts by weight Acetone Emulsifier: 1 part by weight Alkylaryl polyglycol ether To make a suitable formulation of the active compound, 1 part by weight. of the active compound is mixed with the above amount of solvent, the above amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

This active compound formulation is intimately mixed with the soil.

The concentration of active compound in the formulation is of no practical importance; p
Only the weight of active compound per unit volume of soil, given by pm <= qii ), is decisive.

Fill a pot with this treated soil, and add cabbage (Erazzica oLa-ra) to the pot.
Plant ceα)) seedlings. In this way, the active compound is taken up from the soil by the roots of the seedlings and transported to the leaves.

In order to demonstrate the effect within the rhizome, the above experimental animals were infested only on the leaves after 7 days. Furthermore, evaluation is performed by counting or estimating the number of test animals that died on the second day. The action of the active compound in the rhizome is estimated from the mortality status. It is 100% if all the test animals die, and 0% if exactly the same number of test insects as in the untreated control are still alive.

In this test, for example, the compounds of Preparation Examples 1.12 and 17 were tested at 100% concentration at an active compound concentration of 20 ppm.
On the other hand, the Comparative Example Compound (A) had no killing effect at the same concentration (0%).

Example K Threshold Concentration Test/Intrarhizome Effect Test Insect: Myzwz ptrtic
tta) Solvent: 5 parts by weight acetone Emulsifier: 1 part by weight alkylaryl polyglycol ether To make a suitable formulation of the active compound, 1 part by weight of the active compound is mixed with the above amount of solvent and the above amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

This active compound formulation is intimately mixed with the soil.

The concentration of active compound in the formulation is of no practical importance; p
Only the weight of active compound per unit volume of soil, given by pm <=■/It>, is decisive.

Fill a pot with this treated soil, and grow cabbage (Bratzica oleracea) in this pot.
Plant ceα)) seedlings. In this way, the active compound is taken up from the soil by the roots of the seedlings and transported to the leaves.

Evaluation is performed by counting or estimating the number of moving objects. The action of the active compound in the rhizome is estimated from the mortality status. It is 100% if all the test animals die, and 0% if exactly the same number of test insects as in the untreated control are still alive.

In this test, for example, Preparation Example 1.9.12.
Compounds 15 and 17 showed 100% killing at an active compound concentration of 2 appm, while comparative compounds (, 4
) had no killing effect (0%) at the same concentration.

Example L Limit concentration test/nematode test Nematode: MgLoitLo, qy
Solvent: 3 parts by weight acetone Emulsifier: 1 part by weight alkylaryl polyglycol ether To make a suitable formulation of the active compound, 1 part by weight of the active compound is mixed with the above amount of solvent and the above amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

This active compound formulation is intimately mixed with soil heavily contaminated with test nematodes. The concentration of the active compound in the formulation is of no practical importance; only the weight of active compound per unit volume of soil, given in ppm<=g/l), is decisive. Fill pots with this treated soil, plant lettuce, and keep the pots at a temperature of 27°C.

After 4 weeks, the roots of this lettuce are examined for nematode infestation (root galls) and the effectiveness of the active compound is determined in %, with an effectiveness of 100 if the infestation is completely avoided. %, and 0% if the infestation is exactly the same as in controls planted in similarly contaminated untreated soil.

In this test, for example, production example 1.4.6.7
, 8.9.15 and 17 showed 100% efficacy at an active compound concentration of 20 ppm, while the comparator compound CA) gave 0% efficacy at the same concentration.

Example M Limit concentration test/nematode test Nematode: Dalobodella rostochienchus (Gloho
dgra roztochignziz) Solvent = 3 parts by weight of acetate Emulsifier: 1 part by weight of alkylaryl polyglycol ether To make a suitable formulation of the active compound, 1 part by weight of the active compound is mixed with the above amount of solvent; The above amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

This active compound formulation is intimately mixed with soil heavily contaminated with test soil. The concentration of the active compound in the formulation is of no practical importance; only the weight of active compound per unit volume of soil, given in ppm <=η/l), is decisive. The treated bottles are filled into pots, potatoes are planted, and the pots are maintained at a greenhouse temperature of 18°C.

After 6 weeks, the cysts of the potato roots are examined and the effectiveness of the active compound is determined in %.

If parasitism is completely avoided, the effectiveness is 100%.
It is 0% if the infestation is exactly the same as in control seedlings planted in similarly contaminated untreated soil.

In this test, for example, the compounds of Preparation Examples 1 and 17 showed 100% efficacy at an active compound concentration of 20 ppm, whereas Comparative Example Compound (A) gave an efficacy of 0% at the same concentration. Ta.

Claims (1)

[Claims] 1. General formula (I) ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (I) In the formula, R is amino, or alkyl, alkylamino, methylalkylamino, alkoxy, alkenyloxy, and alkylthio. R^1 to R^8 may be the same or different and represent hydrogen, or alkyl, alkenyl, alkoxyalkyl and alkylthioalkyl represents an optionally halogen-substituted group selected from the series consisting of halogen, nitro or dialkylaminoalkyl, or represents an optionally substituted phenyl or benzyl; , the two groups R^1 to R^8 are bonded to 1
Phosphorus-containing heterocyclic compounds may form a monocyclic or bicyclic group which may be substituted with one or more carbon atoms, and n represents 0 or 1. 2. R in the formula is amino, C_1-C_6-alkylamino, methyl-(C_1-C_6-alkyl)-amino or C_1-C_6-alkyl which may be substituted with halogen, C_2-C_6-alkenyloxy, C_1 ~C_6-alkoxy or C_
1 to C_6-alkylthio, R^1 to R^8 may be the same or different, hydrogen, halogen, NO_2, C_1 to C_6-alkyl, C_2 to C_8, which may be substituted with halogen; -Alkenyl, di-(C_1-C_4-alkyl)-amino, C_1-C_4-alkoxy-C_1-C_4-alkyl, C_1-C_4-alkylthio-C_1-C_4
- represents alkyl, benzyl or phenyl, or in which two of the radicals R^1 to R^8, together with the carbon atom or atoms to which they are attached, are substituted by methyl or ethyl; forming a C_5-C_7 cycloalkyl or cycloalkenyl ring which may be cross-linked with a methylene or ethylene group to form a bicyclic group, and n represents 0 or 1. A compound according to claim 1. 3. R in the formula is C_1-C_4-alkyl, C_1-C_6-alkoxy, C_2-C_5-alkenyloxy, C_1-
Represents C_4-alkylthio, C_1-C_4-alkylamino or methyl-(C_1-C_4-alkyl)-amino, R^1 to R^8 may be the same or different, hydrogen, nitro or halogen represents C_1-C_4-alkyl, which may be substituted, or C_1-C_4-alkylthio-C_
1 to C_4-alkyl, or two of the groups R^1 to R^8, together with the carbon atoms to which they are bonded, are bridged by a methylene or ethylene group to form a bicyclic group; 2. The compound according to claim 1, wherein the compound forms a 5- or 6-membered cycloalkyl or cycloalkylene ring, and 1 represents 0 or 1. 4.a) General formula (II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (II) In the formula, Hal represents a halogen, preferably chlorine or bromine, especially chlorine, and R represents a halide having the above meaning. General formula (III) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (III) In the formula, R^1 to R^8 and n have the above meanings, and optionally in the presence of an acid acceptor, and, if appropriate, react in the presence of a diluent, or b) General formula (IV) ▲ Numerical formula, chemical formula, table, etc. ▼ (IV) In the formula, R represents an alkyl that may be substituted. Dithioanhydride is represented by the general formula (V) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(V) In the formula, R^1 to R^8 and n have the above meanings, and X represents a halogen or a general Formula (VI) ▲Mathematical formulas, chemical formulas, tables, etc. are available▼(VI) (where Y represents a substituted alkyl or aryl) alcohol representing a sulfonic acid group, and an appropriate diluent. c) In the first step (as in method a), thiophosphoryl trichloride (PSCl_3) is reacted with the general formula (III
) is reacted with a compound of the general formula (VII) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (VII) In the formula, R^1 to R^8 and n have the above meanings, 2-chloro-1,3 . with the above meaning except that M represents hydrogen or an equivalent amount of an alkali metal or alkaline earth metal (e.g. sodium, potassium or calcium) ion or ammonium ion, optionally in the presence of an acid acceptor. and the general formula (
I) ▲Mathematical formulas, chemical formulas, tables, etc. are available▼(I) Method for producing phosphorus-containing heterocyclic compounds. 5. General formula (
A pest control agent characterized by containing at least one compound of I). 6. General formula (
Use of the compounds of I) for the control of pests, preferably arthropods, in particular insects and arachnids and nematodes. 7. General formula (
A method for controlling pests, characterized in that the compound of I) is applied to pests, preferably arthropods, in particular insects and arachnids and nematodes, or their habitats. 8. General formula (
A method for producing a pest control agent, which comprises mixing the compound of I) with a filler and/or a surfactant. 9. General formula (VII) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (VII) In the formula, R^1 to R^8 may be the same or different, and are hydrogen, alkyl, alkenyl, alkoxyalkyl represents a radical selected from the series consisting of , furthermore, two of the groups R^1 to R^8 may form a monocyclic or bicyclic group which may be substituted together with one carbon atom or heteroatom to which they are bonded. , n represents 0 or 1. 10. Thiophosphoryl trichloride (PSCl_3) is represented by the general formula (III) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (III) In the formula, R^1 to R^8 may be the same or different, represents hydrogen or a group selected from the series consisting of alkyl, alkenyl, alkoxyalkyl and alkylthioalkyl, optionally substituted with halogen, or represents halogen, nitro or dialkylaminoalkyl, or can be substituted a monocyclic ring which represents a certain phenyl or benzyl and which may also be substituted with two of the radicals R^1 to R^8 together with the carbon atom or carbon atoms to which they are bonded; Or, it may represent a bicyclic group, and 1 represents 0 or 1. A general method characterized by reacting with a compound in which 1 represents 0 or 1, appropriately in the presence of an acid acceptor, and optionally in the presence of a diluent. formula(
VII) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (VII) In the formula, R^1 to R^8 have the above meanings.