CS208789B2 - Insecticide,acaricide and nematocide means and method of making the active agent - Google Patents

Abstract

1. N-iso-Propyl-S-(1,6-dihydro-6-(thi)oxo-pyridazin-1- yl-methyl)-thiolphosphoric acid ester-amides of the formula see diagramm : EP0010612,P7,F8 in which R represents alkyl with 1 to 6 carbon atoms and X represents oxygen or sulphur.

Description

The invention relates to insecticidal, acaricidal and nematicidal compositions which contain as active ingredient the novel N-isopropyl-S- [1,6-dihydro-6- (thi) oxopyridazin-1-ylmethyl] thiophosphoric acid ester amides. The invention further relates to a process for the preparation of these new active substances. '

It is already known that certain S- [1,6-dihydro-6-

(thi) oxopyrrolidin-1-yinethyl (thiono) thiophosphoric acid ester amides such as N-allyl-O-ethyl-S- (1,1-dihydro-ethyl-4-oxopyridazin-1-ylmethyl) Thionophosphoric acid esteramide, N, N-dimethyl-O-ethyl-S- (1,6-dihydro-3-methyl-6-oxopyridazin-1-ylmethyl) thiophosphoric acid esteramide and N-isopropyl-n-propyl- S- (1,6-c-ityldio-3-methyl-64-dioxo-pyrrolidin-1-ylmethyl) -thionothiolphosphoric acid esteramide has insecticidal, acaricidal and nematicidal properties (cf. DOS 2 348 736 and 2 603 052). However, the action of these compounds is not always entirely satisfactory, especially at low active compound concentrations and low application rates.

New N-isopropyl-S-

- [1,6-Dihydro-6- (thi) oxopyridazin-1-ylmethyl) Thionothiophosphoric acid ester amides of formula I

X

У N-CH _Z -SP in which

R is C 1 -C 3 alkyl and

X is oxygen or sulfur, and when X is sulfur, R is only a methyl group.

Compounds of formula (I) are prepared by reacting the β-chloromethyl-3-methyl-6- (thi) oxopyridazines of formula (II).

in which

X is as defined above, with the thiophosphoric acid N-isoipropyl ester amide salts of formula III

O OR

II /

M — S — P \

NH-- CsIIy-iso (III) in which

R is as defined above and

M means an alkali metal, alkaline earth metal or ammonium equivalent, optionally using a diluent, at temperatures from 0 to 100 ° C.

The novel compounds of formula I exhibit excellent insecticidal, acaricidal and nematicidal activity.

Surprisingly, the thiophosphoric acid N-isopropyl-S- [1,6-dihydro-6- (thi) oxopyridazin-1-ylmethyl] ester amides of the invention of the general formula I exhibit significantly higher insecticidal, acaricidal and nematicidal activity than prior art compounds of analogous structure and of the same type of effect.

In particular, the invention relates to compounds of formula I wherein:

R represents a straight alkyl group having 1 to 3 carbon atoms and

X is oxygen or sulfur, and when X is sulfur, R is only a methyl group.

If, for example, 1,6-dihydro-1-chloromethyl-3-methyl-6-thioxopyridazine and sodium thiophosphoric acid N-isopropyl-O-methyl ester amide are used as starting materials, the reaction of these compounds can be illustrated by the following reaction scheme:

The 1,0-dihydro-1-chloromethyl-3-methyl-6- (thi) oxopyridazines which are used as starting materials are defined by formula II wherein X is oxygen or sulfur.

The compounds of formula (II) are already known (cf. DOS 2,343,736 and 2,603,052).

Examples include:

1,6-dihydro-1-chloromethyl-3-methyl-6-oxopyridazine and: 1,6-dihydro-1-chloroethyl-3-methyl-6-thioxopyridazine.

The salts of N-isopropyl thiophosphoric acid amides used as further starting materials are defined by formula III. In this formula, the general symbols have the following preferred meanings:

R represents a straight-alkyl group having 1 to 3 carbon atoms and

M is sodium or potassium.

Examples include:

sodium and potassium salts

Thiophosphoric acid O-methyl-6-isopropyl ester amide, sodium and potassium salts

Thiophosphoric acid O-ethyl-N-isopropyl ester amide and the sodium and potassium salts

Thiophosphoric acid O-n-propyl-N-isopropyl ester amide.

The starting compounds of formula III are new.

These compounds of formula III are obtained by reacting N-isopropyl thionophosphoric acid chlorides of formula IV

S OR.

II /

Cl — P

NH-C 3 H 7 -ISO (IV) wherein

R is as defined above and preferably represents a straight alkyl group having 1 to 3 carbon atoms, with at least two equivalents of the hydroxy compound of formula V

M - OH (V), in which:

M is as defined above (preferably sodium or potassium), optionally using a diluent such as water and methanol, at temperatures between 0 and 100 ° C, preferably at 20 to 80 ° C. The reaction products are obtained, for example, by extraction with toluene and evaporation of the aqueous phase under vacuum.

The intermediates of formula (IV) are known or can be prepared analogously to known processes (cf. DOS 2,348,736).

Examples of such compounds include: Ο-methyl-, O-ethyl- and O-n-propyl-N-iso-propyl ester amide chloride.

Examples of such compounds are: Formula V includes sodium hydroxide and potassium hydroxide.

The process for the preparation of thiophosphoric acid N-isopropyl-S- [1,6-dihydro-6- (thi) pyridopyin-1-ylmethyl] ester amides is preferably carried out using suitable solvents or diluents. As such, virtually all inert organic solvents are suitable. These include, in particular, aliphatic and aromatic or chlorinated hydrocarbons such as gasoline, benzene, toluene, xylene, methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers such as diethyl ether and dibutyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl ketone , methyl isopropyl ketone and methyl isobutyl ketone, as well as nitriles such as acetonitrile and propionitrile.

The reaction temperature can be varied within a wide range. In general, the reaction is carried out at temperatures between 0 and 100 ° C, preferably at 20 to 80 ° C.

The process according to the invention is generally carried out at atmospheric pressure.

Per mole of 1, 6-dihydro-1, 4-methyl-6- (thi) oxopyridazine of formula II is generally used between 1 and 6. 0 to 1.2 moles, preferably between 1.05 and 1.15 moles of thiophosphoric acid N-isopropyl ester amides of the formula III.

The reaction is generally carried out in one of the abovementioned diluents and the reaction mixture is stirred for several hours at the desired temperature. Then the reaction mixture? it is diluted with an organic solvent such as toluene and the organic phase is worked up as usual by washing, drying and distilling off the solvent. Refractive index is used to characterize products that are generally obtained in oily form.

The novel Ν4 ^, δορπβ-8- [1,6-dihydro-6- (thi) oxopyridazin-1-ylmethyl] thiophosphoric acid ester amides have, as already mentioned, excellent insecticidal, acaricidal and nematicidal activity. With good phytotoxicity they have a good effect against absorbent and voracious insects as well as against mites and nematodes.

The compounds of the formula I according to the invention can therefore be used successfully in plant protection as pest control agents.

The active substances have good plant compatibility and favorable warm-blooded toxicity and are suitable for controlling pests, especially insects, spider mites and nematodes in agriculture, forestry, · protection of stocks and materials, as well as hygiene. They are effective against normally susceptible and resistant species as well as against all or only individual stages of development of pests. The above mentioned pests include:

from the order of the Isopods, for example Oniscus asellus, Armadillidium vulgarej, Porcellio scaber;

from the class of the Diplopoda, for example the blind millipede (Blaniulus guttulatus);

from the Chilopoda class, for example Geophilus carpophagus, Scutigera spec,];

from the centipede class (Symphyla), for example

Scutigerella inumaculata;

from the order of the Thysanura, for example Lepisma saccharina;

from the order of the Collembola, for example Onychiurus armatus; from the order of the Orthoptera, for example the cockroach (Blatta orientat-s), the cockroach (Periplaneta americana), Leucoiphaea maderae, the Russian cockroach (Blattella germanlca), the cricket (Acheta domesticus), the mole cricket (Gryllota-pa spec. ), Locusta migratoria migratcricides,

Melanoplus differentialis, Schistocerca gregaria;

from the order of the Derrnaptera, for example Forficula auricularía;

from the order of the Isoptera, for example Reticulitermes spec.

from the order of the lice (Anoplura), for example, the tree frog (Phylloxera vastatrix), the sage (Pemphigus spec.), the louse (Pediculus humanus corporis), Haematopinus spec.

Linognathus spec .;

from the order of the Mallophaga, for example the Trichodectes spec.

Damalinea spec .;

from the order of the Thysanoptera, for example Hercinothrips femoraliis, Thrips tabaci;

of the order Heteroptera, for example Eurygaster spec.

Dysdercus intermedius, Beetle (Piesma quadrata), Bed Bug (Cimex lectularius), Rhodnius prolixus,

Triatoma spec .;

from the order of the winged hoe (HoímDq ^ te ^ ua), for example, Aleurodes brassicae, Bemisla tabac ', Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae (Cryptus ribis) , aphid aphid (Doralis fabae), apple aphid (Doralis pomi), bloody aphid (Eriosoma lanigerum), aphid (Hyalopterus arundinis), Macrosiphum avenae,

Myzus spec., Hop Aphid (Phorodon humuli), Aphid Aphid (Rhopalosiphum Pad), Tufted Emperor (Empoasca spec.), Euscelis bilobatus

Nephotettix cincticeps,

Lecanium corni, Saissetia oleae,

Laodelphax striatellus,

Nilaparvata lugens,

Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spec., Psylla spec., Lepidoppera, for example

Pectinophora gossypiella, Dark-spot Carpet (Bupalus pírnarius), Cheimatobia brumata, Apple Keyhole (Lithocolletis blancardella), Apple Moth (Hyponomeuta padella), Plutella maculipennis Lymantria spec.), Bucculatrix thurberiella, Fylloc.nistis citrella, Agrotis spec., Euxoa spec.

Feltia spec.,

Earias insulana, Heliothis spec., Laphygma exigua, Cabbage moth, Panolis flammea, Prodenia litura,

Spodoptera spec. Trichoplusia ni

Carpocapsa pomonella, White (Pieris spec.), Chilo spec., Corn borer (Pyrausta nubilalis), Meal moth (Ephestia kuhniella), Wax moth (Galleria mellonella), Carpet moth (Cacoecia podana),

Capua reticulana,

CLl (cгistcneura fumiferana)

Clysia ambiguella, Hornona magnanima, Tortrix viridana, from the order of the beetles (Coleoptera), for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus alder (Agelastica alni), leaf beetle (Leptinotarsa decemlineata), leaf beetle (Phaedon cochleariae),

Diabrotica spec., Psylliodes chrysocephala,

Epilachna varivestis, Atornaria spec., Oryzaephilus surinamensis, Anthonomus spec., Sitophilus spec., Otiorrhynchus sulcatus,

Cosinopolite.s sordidus, Ceuthorrhynchus assimilis,

Hypera, Dermestes spec.

Trogoderma spec., Anthrenus spec., Atta-genus spec., Lyctus spec., Meligethes aeneus, Ptinus spec., Niiptus hololeucus, Gibbium psylloides, darkling beetle (Tribolium spec.), Darkling beetle (Tenebrio molitor), blacksmith (Agriotes spec.),

Conderus spec., Common Cockchafer (Melolontha melolontha) Common Cockchafer (Amphimallon solstitialis),

Costelytra zealandica, of the order Hymenoptera, for example Diprion spec., Hoplocampa spec., Lasius spec., Monomorium pharaonis, Vespa spec., For example Diptera, e.g. mosquito (Aedes spec.), anofeles (Anopheles spec.), mosquito (Culex spec.), fruit fly (Drosophila melanogaster), fly (Musea spec.), sunflower (Fannia spec.), buzzard (Calliphora erythrocephala), buzzer (Lucilia spec.), Chrysomyia spec., Cuterebra spec., Hamster (Gastrophilus spec.), Hyppobosca spec., Thistle (Stomoxys spec.), Hamster (Oestrus spec.), Hamster (Hypoderma spec.), Horsefly (Tabanus spec.) .), Tannia spec., Garden Fly (Bibio hortulanus), Barberry (Oscinella frit), Phorbia spec., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, z of the order Slphonaptera, for example, the flea (Xenopsylla cheopis), flea (CeratQphyllus sp ec.), of the order Arachnida, for example

Scorpio maurus, Latrodectus mactans, from the order of the mites (Acarina), for example Acarus moss, Argas spec., Ornithodoros spec., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, tick (Boophilus spec.), drinker (Rhipicephalus spec.), drinker (Amblyomma spec.), Hyalomma spec., tick (Ixodes spec.), flesh (Psorcptes spec.), scab (Chorioptes spec.), Sarcoptes spec. ., Mites (Tarsonemus spec.), Currant Spider (Bryobia praetiosa), Spider Mite (Panonychus spec.), Spider Mite (Tetranychus spec.).

The nematodes harmful to plants include the genera:

Pratylenchus spec., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spec.

Meloidogyne spec., (Aphelenchoides spec.), Lcngidorus spec.,

Xiphineima spec., Trichodorus spec.

The active compounds can be converted into the customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granulates, aerosols, natural and synthetic substances impregnated with the active compounds, small particles coated with polymeric substances and coating materials for seeds, flammable additives such as smoke cartridges, smoke jars, smoke spirals and the like, as well as compositions in the form of concentrates of the active substance for cold or hot mist dispersion.

These compositions are prepared in a known manner, for example by mixing the active ingredient with fillers, i.e. liquid solvents, with liquefied gases under pressure and / or solid carriers, optionally using surfactants, i.e. emulsifiers and / or dispersants and / or foaming agents. If water is used as a filler, it is also possible to use, for example, organic solvents as co-solvents. Basically suitable liquid solvents are: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethylsulfoxide, and water. By liquefied gaseous fillers or carriers is meant those liquids which are gaseous at normal temperature and pressure, for example aerosol propellants, such as halogenated hydrocarbons, as well as butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are: natural stone meal, such as kaolins, alumina, talc, chalk, quartz, attaipulgite, montmorillonite or diatomaceous earth, and synthetic stone meal, such as highly disperse silica, alumina and silicates. Crushed and fractionated natural stone materials such as limestone, marble, pumice, sepiolite and quarry, as well as synthetic granules of inorganic and organic flours, and granules of organic material, such as sawdust, are suitable carriers for the preparation of granulates, coconut shells, corn cobs and tobacco stems. Suitable emulsifiers and / or foaming agents are non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, fatty alcohol polyoxyethylene ethers, e.g.

The compositions of the invention may include adhesives such as carboxymethylcellulose, natural and synthetic powdered, granular or latex polymers such as gum arabic, polyvinyl alcohol and polyvinyl acetate.

In addition, these compositions may contain coloring agents such as inorganic pigments such as iron oxide, titanium dioxide and ferrocyanide blue, and organic dyes such as alizarin dyes and metallic azo-phthalocyanine dyes as well as trace elements such as iron, manganese, boron salts. ,, copper, cobalt, molybdenum and zinc.

The concentrates generally contain between 0.1 and 95% by weight, preferably between 0.5 and 90% by weight, of active ingredient.

The active compounds according to the invention can be used in the form of commercial preparations and / or in dosage forms prepared from these preparations.

The active compound content of the dosage forms prepared from the commercial preparations can be varied within wide limits. The concentration of the active ingredient in the dosage forms can be from 0.0000001 to 100% by weight, preferably from 0.01 to 10% by weight.

The application is carried out in a conventional manner adapted to the application form used.

When used against hygiene pests and against storage pests, the active compounds according to the invention are distinguished by an excellent residual effect on wood and clay and good stability to alkali on lime substrates.

Example A

Test limit concentration / nematode test nematode: nematode · .Meloidogyne incognita solvent:

parts by weight of acetone emulsifier:

part by weight of alkylaryl polyglycol ether

To prepare a suitable active ingredient, 1 part by weight of active ingredient is mixed with the indicated amount of solvent, the indicated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

The active agent is thoroughly mixed with soil heavily contaminated with test nematodes. The concentration of the active ingredient in the composition plays practically no role, only the amount of active ingredient per unit volume of soil, which is given in ppm, is critical. The treated soil is filled with pots, lettuce is sown in the soil and the pots are kept in a greenhouse at 2 ° C.

After 4 weeks, the roots of nematode lettuce are rooted and the effect of the active compound evaluated in%. The effect is 100% if the attack is completely prevented and 0% if the infestation is exactly as high as that of control plants growing in untreated but contaminated soil.

The active substances, the amounts used and the results are given in Table A below:

Table A

Meloidogyne incognita limit test Active substance Mortality in% at 5 ppm drug concentration

-SP ^x nh-ch ₂ ch-ch _of (known) сн _ъ

A-ch _of sp \

NH- & iso

100%

Q OCH3 <

^N NH'C ₃ W _? Uo

100%

II

ΝΗΗ- ^ ίΜ

Test for leaf beetle larvae (Phaedon cochleariae) solvent:

parts by weight of acetone emulsifier:

part by weight of alkylaryl polyglycol ether

In order to prepare a suitable active ingredient, 1 part by weight of the active ingredient is mixed with the indicated amount of solvent and the stated amount of emulsifier and diluted to 100% with water to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by immersion in an active preparation of the desired concentration and. the leaves thus treated shall be occupied by the larvae of the leaf beetle [Phaedon cochleariae] if they are still wet.

After the required time, the mortality at why is determined. 100% means that all larvae have been killed and 0% means that no larvae have been killed.

In this test, for example, the following compounds of the invention exhibit higher efficacy than those known in the art [cf. Table B):

Table В

Mortality in% after 3 days

Phaedon larvae test

Active substance concentration in%

Active substance

0,1 100

0.01 0 (known)

0,1 100

0.01 0

--CH 3 -S — P z \ s

CH

o CH ₃ ¹

-CH 1 -S-Ρζ

NH-C ^Hj í

0,1 100

0,01 100

o.i íoo

0,01 100

0,1 100

0,01 100

N-CHrS-P '

NH-Cl 2

0,1 100

0,01 100

Example C

Test for resistant spider mite (Tetranychus urticae) solvent:

parts by weight of acetone emulsifier:

part by weight of alkylaryl polyglycol ether

To prepare a suitable active ingredient, 1 part by weight of the respective active ingredient is mixed with said amount of solvent and said amount of emulsifier, and the concentrate is diluted with water to the desired concentration.

Bean plants (Phaseolus vulgaris), heavily infested with all developmental stages of the spider mite (Tetranychus urticae), are treated by immersion in the preparation of the active compound at the desired concentration.

Mortality in ° / o is determined after appropriate time,

100% means that all spider mites have been killed, 0% means that none of the mites have been killed.

T a b at 1 k and C

Mortality in% after 2 days

Active substance concentration in%

In this test, for example, the following compounds of the invention show a better effect of the known compound (cf. Table C):

Test for resistant strain of spider mite (Tetranychusj)

WITH

S 0C ₃ H

0,1 20

0.01 0 (known j

0,1 60

0.01 0 (known) (known)

GH ₃

OCf

NH-C 1-6

0,1 70

0,01 20

0,1 100

0,01 100

CH,

0,1 106

0.01 40 s

ch ·,

0.1

0.01

100 сн _ъ

0.1

0.01

100 ALIGN!

Example D

Lightning test (Laphygma) solvent:

parts by weight of acetone emulsifier:

part by weight of alkylaryl polyglycol ether

To prepare a suitable active ingredient, 1 part by weight of the active ingredient is mixed with said amount of solvent and said amount of emulsifier and the concentrate is diluted with water to the desired concentration.

Leaves of cabbage (Brassica) oleracea) are treated by immersion in the active agent of the desired concentration and occupied with caterpillars (Laphygma frugiperda) while still wet.

After the required time, the mortality at why is determined. 100% means that all the caterpillars were killed, while 0% means that none of the caterpillars were killed.

In this test, for example, the following compounds of the invention have a better effect than the prior art:

Table D

Laphygma Test

Active substance

Active substance concentration in%

Mortality in% after 3 days

0,1 75

0.01 0

0,1 100

0,01 70

9 _x and ₅

P

Poppy Aphid Test (Doralis fabae) Solvent:

parts by weight of acetone emulsifier:

part by weight of alkylaryl polyglycol ether

0,1 100

0.01 90 concentrations are poured over bean plants (Vicia faba) which are heavily attacked by poppy (Doralis fabae) so that the active agent penetrates the soil without wetting the above-ground part of the plant. The active substance is taken up by the roots and from there it is transported to the shoot.

After the required time, the mortality at why is determined. 100% means that all aphids have been killed, while 0% means that no aphids have been killed.

In this test, for example, the following compounds of the invention show a higher effect than the compound known in the art.

To prepare a suitable active ingredient, 1 part by weight of the active ingredient is mixed with said amount of solvent and said amount of emulsifier, and the concentrate is diluted with water to the desired concentration.

In each case 20 ml of the active agent required

Table E

Poppy Aphid Test (Doralis fabae) - Systemic Effect

Active Ingredients Concentration Mortality% in% of active ingredients in% 4 days

CHA s

0.1

Examples of illustrative substances:

EXAMPLE 1 The method of production was 0.1

íí)

15.8 g (0.1 mol) of 1,6-dihydro-1-chloromethyl-3-ethyl-6-oxopyridazine and 24.3 g (0.11 mol) of potassium thiophosphoric acid O-ethyl-N-isopropyl ester ester are heated in 200 ml. ml of acetonitrile at 50 ° C for 13 hours, and then the reaction mixture is washed with · 500 ml of toluene. The toluene solution is washed with 50 ml of a saturated solution. sodium bicarbonate, dried over sodium sulfate and then evaporated. 25 grams (82% of theory) of thiolphosphonic acid amide O-ethyl-N-isopropyl-S- (1,6-dihydro-3-methyl-6-oxopyridazinylmethyl) ester are obtained as a yellow oil of refractive index. n _D ²² = · 1.5396.

The following compounds were prepared in an analogous manner:

yield:

° / o theory, refractive index: n ₀ 21i = 1.6031

yield:

% of theory, refractive index: n _D ²² - 1.5280 (2) (3) yield:

° / o theory, refractive index:

n _D ²² = 1.5495

20878 »

The alkali metal thiophosphoric acid ester amides used as starting materials can be prepared, for example, as follows:

Example a

ОС3Н7-П

II // pcs — p \

NH — C3H7-1SO (4)

Mixture of 150 ml of water, 100 ml of methanol, 61,6 grams (1,1 mol) of potassium hydroxide and

107.8 g (0.5 mol) of thionothiophosphoric acid O-propyl ester-N-isopropylamide are refluxed for 1 hour and then cooled to room temperature. The solution is extracted with 200 ml of toluene, the aqueous phase is separated and evaporated to dryness in vacuo. The residue is triturated with acetone, filtered off

Claims (2)

PREDMST An insecticidal, acaricidal and nematicidal composition, characterized in that it contains at least one thiophosphoric acid N-1-isopropyl-S- (1,6-dihydro-6- (thi) oxopyridazin-1-ylmethyl) esteramide as an active ingredient. of formula I wherein R is C 1 -C 3 alkyl and X is oxygen or sulfur, and when X is sulfur, R is only a methyl group. 2. A process for the preparation of an active ingredient according to claim 1, which comprises dissolving the residue of 1,6-dihydro-1-chloromethyl-3-methyl-6- (thi) oxopyridazines of the formula II and distilling off the filtrate. solvent under vacuum. There was left 59 g (53 why) of the potassium salt of O-n-propyl-N-isopropyl thiophosphoric acid amide, m.p. 144-100C. The following compounds can be prepared in an analogous manner: O OC2H5 KS — P \ NH — C3H7-ISO (6) O OCH3 KS — P \ NH-C 3 H 7 -ISO (7) wherein X is as defined above, acting with the salts of the N-isopropyl ester amides of thiophosphoric acid of formula III O OR IH M — S — P \ NH - C 3 H 7 -ISO (IIIJ, in which R is as defined above, M is an alkali metal, alkaline earth metal or ammonium equivalent, optionally using a diluent at temperatures between 0 and 100 ° C.