DE2007239A1 - Pyrimidine derivatives and their use - Google Patents

Description

PATENT LAWYERS Dr. D. Thomsen

Dipl.-Chem.

H. Tiedtke

Dipl.-Ing.

G. Buehling

Dipl.-Chem.

8000 MONKS 2

VAL 33

TELEPHONE 0811/226894

TELEGRAM ADDRESS: THOPATENT

MÖNCHEN February 17, 1970 case PP 21718 / T 3488

Imperial Chemical Industries Limited London / Great Britain

Pyrimidine derivatives and their use

The invention relates to new pyrimidine derivatives, processes for their production, preparations containing them and on methods of combating plant diseases.

British patent application 14 272/66 describes 2-amino-substituted pyrimidine derivatives for pest control .

According to the invention are a pyrimidine compound of the formula

, 009838/2250

TMMm, NNrfM MMfUIeMr lMtttlgune

and their acid addition salts are provided, where R _{1 and R 2 represent} hydrocarbon groups,

Rq and R _{4 represent} hydrogen or halogen atoms, substituted or unsubstituted hydrocarbon groups, or R and R together represent an alkylene bridge group and R _{5 represents} a hydrogen atom or a hydrocarbon group

represents.

Preferred hydrocarbon groups are alkyl, alkenyl, aryl and alkaryl groups.

Furthermore, in an embodiment according to Invention a pyrimidine compound of the formula

^R 4

and their acid addition salts are provided, where R _{1 and R 2 represent} alkyl or aryl groups,

R ₃ and R _{4 represent} hydrogen or halogen atoms or are substituted or unsubstituted alkyl, alkenyl or aryl groups or together are an alkylene bridging group

represent and

R _{5 represents} a hydrogen atom or an alkyl group.

009836/2250

In particular, according to the invention, a compound of the formula

y N

^R 2

^HR 5

in the

R ₁ and R _{2 represent} alkyl groups or phenyl groups, which may optionally be substituted, and R ₃ , R ₄ and Rr represent hydrogen atoms or alkyl, alkenyl, aryl or aralkyl groups, the aryl groups in the latter two groups being optionally substituted , and their acid addition salts are provided.

As a suitable size for the RpR--, ^R 3 * "' ^R 4 ~ or R ₅ group, if it represents an alkyl group, for example an alkyl group with not more than 10 carbon atoms, in particular a lower alkyl group, ie a An alkyl group with no more than 6 carbon atoms, for example a methyl, ethyl, n-propyl, η-butyl or n-amyl group.

In a preferred embodiment according to the invention become a pyrimidine compound of the formula

009836/2250

and their acid addition salts are provided, wherein

R. and R, are lower alkyl groups,

R _{5 is} a hydrogen atom or a lower alkyl group

and where either

(1) R, a hydrogen or halogen atom, a lower alkyl or alkenyl, benzyl or lower cyanoalkyl group and R. is a hydrogen atom, a lower alkyl or phenyl group or

(2) R ₃ and R ₄ together represent a tri- or tetramethylene bridging group. Particularly preferred compounds are those with the latter formula, where R, and R_ are lower alkyl radicals, R and R _{4 represent} hydrogen atoms or lower alkyl or lower alkenyl groups or together form an alkylene bridge, Rg is a lower alkyl group.

Specific pyrimidinyl carbamates according to the invention, which have been found to be particularly useful are summarized in Table I below. The connections all correspond to the general formula

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the various substituent groups R ₁ R ₃ N, R-, R and R _{5 of} each compound being indicated in columns under appropriate headings in Table I along with the melting points (FP.) expressed in degrees C.

Table I.

link
No. V H \ ^B 5 FP. 1 ^CHJ > H CH, CH, 99 ° 2 -'S ,. CH, CH, 81 ° ^6H 5 \
< CH, CH, B. 164 ° 4th CH, CH, 156 °

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Table I (continued)

link
No. > ^R 3 3 Cl ^R 4 ^R 5 FP. 5 -CH ₂ CH ₂ -3 ⁰ A 112 ° 6th ch / CHj CHj 131 ° 7th CH CH ₂ - CHj 145 ° ch / -CH ₂ CH ₂ CR CHj / 2 * Q • r 8 ^: ·; ⁰⁸ ^ s. -A CHj CHj 136 ° 3 · K-
CH./ -A CHj H 91 ° 10 CHj CHj 7 «° 11 .CHj ⁰ A 79 °

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Table I (continued)

link
No. R ₁ R ₃ ^R 4 ^R 5 12th CH ^ CH ₃

FP.

viscous

The compounds of numbers 2, 3, 4 and 8 in table I are particularly useful for pest control.

In the present context, the pyrimidine ring is numbered as follows:

It should be emphasized that the 4- and 6-positions are equivalent.

The compounds according to the invention are relevant to various insect pests including the following very poisonus:

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Tetranychus telarlus (red leaf spider mite) Aphis fabae (black aphid) Pierifl brasaicae (white cabbage caterpillar) Megoura viciae (green aphid) Phaedon coohleariae (mustard beetle) Mus ca domestioa (house fly) Meloidogyne incognita (nematodes)

The compounds according to the invention also have activity against many different fungal diseases, e.g. the following specific diseases:

Erysyphe graminis (powder mold) on wheat Erysyphe graminia (powder mold) on barley Puccinia recondita (rust) on wheat Phytophthora infestans (later Brand) on tomatoes Sphaerotheca fuliginea (powder mold) on cucumbers Podosphaera leucotricha (powder mold) on apples

üncinula necator (powder mold) on wine

Piricularia oryzae (Meltau) on rice Piasmopara viticola (frost mold) on wine Venturia inaequalis (scab) on apples

Certain compounds according to the invention also have activity against molluscs.

In a further embodiment according to the invention, pest control preparations are provided which

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as active ingredient a pyrimidine compound of the formula

N-C-O

or their acid addition salts, where R _{1 and R 2}

Represent hydrocarbon groups, R ₃ and R. represent hydrogen or halogen atoms, substituted

or represent unsubstituted hydrocarbon groups

R ₃ and R. together represent an alkylene bridging group

and Rc represents a hydrogen atom or a hydrocarbon group

represents.

Suitable size of the R, -, R ₂ "* ^R 3 ~ ^'R 4 ~ ^{and R5} ~ group, if it represents a hydrocarbon group, for example, an alkyl group of 10 carbon atoms are considered not more than, in particular a lower alkyl group, ie, an alkyl group with no more than 6 carbon atoms, for example a methyl, ethyl, n-propyl, n ~ butyl or n-amyl group.

In a preferred embodiment according to the invention, pest control preparations are provided which contain a pyrimidine compound as the active ingredient. formula

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ο R ₃

in the

R, and R _{2 are} lower alkyl groups,

R _{5 is} hydrogen or a lower alkyl group and either

(1) R _{3 is} a hydrogen or halogen atom, a lower alkyl, alkenyl, benzyl or lower cyanoalkyl group, Ri is a hydrogen atom, a lower alkyl or phenyl group or

(2) Ra and R ₄ together represent a tri- or tetramethylene bridging group, or contain their acid addition salts.

The compounds and preparations according to the invention can be used for agricultural or horticultural purposes; the compound or type of preparation used in any case will depend on the particular purpose for which it is to be used.

Preparations containing compounds according to the invention may be in the form of dusting powders or granules, the active ingredient being mixed with a solid diluent or a carrier. Suitable

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Suitable solid diluents or carriers can be e.g. kaolin, Bentonite, diatomite, dolomite, calcium carbonate, talc, powdered Magnesium oxide, Fuller's earth, gypsum, Hewitt's earth, diatomaceous earth and china clay. Preparations for coating of seeds can contain, for example, an agent that promotes the adhesion of the preparation to the seed, e.g. a mineral oil.

The preparations can also be in the form of dispersible powders or granules which, in addition to the active ingredient contain a wetting agent to facilitate dispersion of the powder or granules in liquids. Such Powders or granules can contain fillers, suspending agents, and the like.

The preparations can also be in the form of liquid approaches to be used as baths or sprays, with it is generally aqueous dispersions or emulsions which the active ingredient in the presence of one or more Contain wetting agents, dispersants, emulsifiers or suspending agents.

Wetting agents, dispersants and emulsifiers can be cationic, anionic or non-ionic. Suitable Cationic type agents include, for example, quaternary ammonium compounds such as cetyltrimethylammonium bromide. Suitable agents of the anionic type are, for example, soaps, salts

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aliphatic monoester of sulfuric acid, such as sodium lauryl sulfate, Salts of sulfonated aromatic compounds, such as sodium dodecylbenzenesulfonate, sodium, calcium or ammonium lignosulfonate, Butyl naphthalene sulfonate and a mixture of sodium salts of diisopropyl and triisopropyl naphthalene sulfonic acids.

Suitable agents of the non-ionic type are e.g. the condensation products of ethylene oxide with fatty alcohols, such as oleyl alcohol or cetyl alcohol, or with alkylphenols, such as octylphenol, nonylphenol and octy ^ cresol. Others not - Ionic agents represent the partial esters derived from long chain fatty acids and hexitol anhydrides, the Condensation products of the partial esters with ethylene oxide and the lecithins.

Suitable suspending agents are, for example, hydrophilic colloids such as polyvinylpyrrolidone and sodium carboxymethyl cellulose, and vegetable rubbers such as gum acacia and gum tragacanth.

The aqueous dispersions or emulsions can be prepared by adding the active ingredient or ingredients be dissolved in an organic solvent which contain one or more wetting agents, dispersants or emulsifiers can, and then the mixture obtained in this way is added to water, which also contains one or more network,

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May contain dispersants or emulsifiers. Suitable organic solvents are ethylene dichloride, isopropyl alcohol, propylene glycol, diacetone alcohol, toluene / kerosene, Methylnaphthalene, xylenes and trichlorethylene.

The preparations to be used as sprays can also be in the form of aerosols, the approach in kept under pressure in a container in the presence of a propellant such as fluorotrichloromethane or dichlorodifluoromethane will.

The compounds according to the invention can also be formulated in preparations with capsules or microcapsules, which contain either the active ingredient itself or a preparation containing an active ingredient and after any the known encapsulation or microencapsulation techniques.

By including suitable additives (for example to improve distribution, adhesion and resistance to rain on treated surfaces), the various preparations can be better adapted to the various purposes for which they are used.

The pyrimidine derivatives can also expediently be prepared by mixing them with fertilizers

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will. A preferred preparation of this type are granules of fertilizer material including inclusions (e.g. in the form of a Coating) of a pyrimidine derivative. The fertilizer material can, for example, contain nitrogen or phosphate substances contain.

In a further embodiment according to the invention ^ invention, a fertilizer is provided which contains a pyrimidine compound as defined above.

The preparations which are to be used in the form of aqueous dispersions or emulsions are generally applied in the form of a concentrate which contains a high proportion of the active ingredient or active ingredients, the concentrate being diluted with water before use. In the case of these concentrates, it is often necessary that they withstand prolonged storage times and, after such storage, can be diluted with water to form aqueous batches which remain homogeneous for a sufficient time so that they can be applied by conventional spray devices. The concentrates can expediently contain 10 to 85% by weight of active ingredient or active ingredients and generally 25 to 60% by weight of active ingredient or active ingredients. When diluted to form aqueous compositions, such compositions may contain varying amounts of active ingredient or ingredients depending on the purpose for which they are used

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are to be used, but an aqueous batch with a content of 0.001 to 1.0 wt. S or active ingredient Active ingredients are used.

It goes without saying that the preparations according to the invention, in addition to the pyrimidine derivative, have one or more others May contain compounds with biological activity.

A particularly useful characteristic of the activity of compounds according to the invention is their ability as systemic pesticides to act, i.e. its ability to act in a plant to fight an infection or a Infestation to invade on the same remote from the place of the original order of a compound. So can a compound according to the invention or a preparation containing them on the soil of the roots of a plant surrounds, applied v / ground and taken up by the plant through its roots to control pests on the plant will.

When using pyrimidine compounds or preparations containing them, several Paths to be taken. So you can in a suitable manner directly on the foliage of the plant or on their infected and / or infested areas are applied;

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alternatively, the soil surrounding the plant or soil / are sown or planted in the seeds or plants, with the pyrimidine compounds or with preparations containing them be treated. If desired, the seed itself can be treated in the same way.

Furthermore, according to the invention, a method for

™ Combating unwanted insect and fungal infections provided by plants, with a pyrimidine compound as defined above or on the location of the plant a preparation defined above is applied.

In a further method according to the invention for combating insects and fungal infections of plants applying a pyrimidine compound as defined above or an above de- ψ finiertes preparation to a plant or to seeds thereof.

Furthermore, according to the invention, a method for treating agricultural soil is provided, wherein a pyrimidine compound as defined above or a preparation as defined above is applied to the soil will.

Another feature of compounds according to the invention is their ability to kill molluscs, e.g. Snails.

0 0 9836/22 50

Also in accordance with the invention is a method for the control of mollusks provided / v / obei on the whereabouts of the mollusks an above-defined Pyrimidine compound or a preparation defined above is applied.

The invention is explained in more detail below by means of examples.

example 1

This example illustrates the preparation of 2-ethylamino-4-methyl-6-pyrimidinyldimethylcarbamate ( compound no.2 in Table I) having the structure:

N-C-O

H CH ₂ CH ₃

3.5 ml of dimethylcarbamoyl chloride were added to a mixture of 4.8 g of 2-ethylamino-4-hydroxy-6-methyl- pyrimidine, 4.5 g of anhydrous potassium carbonate and 60 ml of ethyl acetate; the whole was refluxed for 6 hours. 60 ml of methylene dichloride were added; the insoluble material was removed by filtration. The filtrate was

00SI36 / 22S0

Washed with a 1% aqueous sodium hydroxide solution and then with water and over anhydrous sodium sulfate
dried. The solid was filtered off, the solvent was removed by evaporation and the residue was removed
Ether recrystallized; 2-Ethylamino-4-methyl-6-pyrimidinyldimethylcarbamate fell as a white solid with a
Melting point of 81OC.

Example 2

The compounds with the numbers 1 and 3 to 12 were prepared by a method similar to that in Example 1, the appropriate reactants were used in each case. The melting points of these compounds are given in Table I above.

Example 3

This example illustrates a concentrate with a miscible oil that can easily be converted into a liquid formulation suitable for spraying purposes by dilution with water. The concentrate has the following
Composition:

Compound No. 1 of Table I 25.0% by weight

¹¹ LUBROL ^M L (alkylphenol / ethylene oxide condensate;

"LUDROL" is a Karenzelchen) 2.5 "

Calcium dodecylbenzenesulfonate 2.5

"AROMASOL" I! (Alkylbenzene solvent;.
• Aromaeol "is a commodity oak) '· 70 * 0 "

100.0 ·

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Example 4

This example also explains a concentrate in the form of a miscible oil. The composition of this concentrate is the following:

Compound No. 2 of Table I 25.0% by weight

"LUBROL" L ("Lubrol" is a trademark) 4.0 "Calcium dodecylbenzenesulfonate 6.0"

"AROMASOL"HC'Aromasol"is a trademark) 65.0 "

100.0 "

Example 5

This example illustrates a wettable powder with the following composition:

Compound No. 3 of Table I Sodium Silicate
Calcium lignosulfonate china clay

Example 6

This example illustrates an atomizable liquid with a mixture of 25% by weight of Compound No.

of Table I and 75 wt% xylene.

Example 7

This example illustrates a dusting powder that is applied directly to plants or other surfaces and 1% by weight of compound no. 5 of

0 0 98 367.22 5 0

25.0 Wt% 5.0 Il 5.0 Il 65.0 Il 100.0 Il

Table I and 99 wt% talc.

There were 25 parts by weight of Compound No. 6 of Table I, 65 parts by weight of xylene and 10 parts of a Alkylaryl polyether alcohols ("Triton" X-100; "Triton" is a trademark) are mixed in a suitable mixer. There was thus obtained an emulsion concentrate which was mixed with water to make an emulsion suitable for use in agriculture.

Example 9

There were 5 parts by weight of compound no. 7 of Table I carefully in a suitable mixer 95 parts by weight of talc mixed. In this way a dusting powder was obtained.

Example 10

10 parts by weight of compound no. 8 from Table I, 10 parts of an ethylene oxide / octylphenol condensate ("Lissapol"NX;"Lissapol" is a trademark) and HO CuwichtiJtoile diacetone alcohol were carefully prepared, on various uc wines, was obtained in a concentrate which, according to Minchon and Kns.sor, gave an aqueous dispersion suitable for use as a spray in the inoculation of insect

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Is suitable for pests.

Example 11

This example illustrates a concentrated liquid formulation in the form of an emulsion. The below compiled Ingredients were mixed together in the amounts indicated and the whole was made into a solution ™ the ingredients stirred.

Compound No. 9 of Table I.

"LUBROL" L ("Lubrol" is a trademark)

Calcium dodecylbenzenesulfonate, ethylene dichloride

¹¹ AROMASOL "H (" Aromasol "is a trademark)

20th Wt% , Il 17th 3 Il 45 Il 15th Il 100 Il

Example 12

There were the ingredients compiled below in the specified amounts for the preparation of a Grind a powder mixture that is easily dispersible in liquids.

Connection ur. 10 from Table I. 50 Weight Dispersol T 5 Il China clay 45 Il 100 Il

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Example 13

A preparation was made in the form of granules easily dispersible in liquids (e.g. water), by grinding the first 4 of the components listed below together in the presence of water and then sodium acetate was mixed in. The mix was dried and passed through a standard UK machined sieve (Size 44 to 100) given to achieve the desired grain size.

Compound No. 11 of Table I 50% by weight

Disnersol T Goulac

Calcium Dodecylbenzenesulfonate Sodium Acetate

Example 14

A preparation suitable for use as a seed coat was made by all 3 below specified ingredients were mixed in the specified amounts.

Compound No. 12 of Table I, China Clay Mineral Oil

100

12, 5 It 5 Il 12, 5 Il 20th Il 100 Il

80 Weight 2 Il Eat M.

0 0 9 0 1 B / 2 2 S 0

Example 15

A granular preparation was prepared by dissolving the active ingredient in a solvent, the obtained Sprayed solution on grains of pumice stone and allowed the solvent to evaporate.

Compound No. 12 of Table I 5% by weight

Pumice grains 95 "

lÖÖ " Example 16

A mixed batch was prepared by adding the ingredients listed below to the ones indicated Quantities have been mixed and ground.

Compound No. 4 of Table I 40% by weight

Goulac IO "

Water 50 "

TÖÖ "

Example 17

This example illustrates a preparation that can be used to combat suitable for snails. The ingredients listed below were used in the amounts indicated mixed and then converted into pellets.

Connection ur. B from Tabnlle 1 4.0 Gev /.-%

Bran odor VJcUz en !; ei ml Ingo (whentinij; *) ΟΓ., 0

0 09836/2250

Example 18

The toxicity of a number of compounds according to the invention to various insect pests has been studied; the tests carried out and the results obtained are given below. The compounds according to the invention were used in each case in the form of liquid batches containing O _r 1% by weight of the compound. The batches were prepared by dissolving each compound in a solvent mixture consisting of 4 volumes of acetone and 1 volume of diacetone alcohol. The solutions were then diluted with water containing 0.01% by weight of a wetting agent (sold under the trade name “LISSAPOL” NX) until the liquid batches had the required concentration of the compound (“LISSAPOL” is a trademark).

The test procedure chosen with respect to each test insect was basically the same and consisted of placing a number of the insects on whatever medium could be a host plant or food on which the insect feeds and the insect and / or medium with it treated the approaches. The insect mortality was then determined for periods varying from one to three days after treatment.

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The results of the tests are given in Table II below. The first column of this table gives the connection used. The following columns each give the name of the test insect, the host plant or the medium to which it was applied and the number of days that could elapse after treatment, before determining the percentage of insects killed. The determinations are in whole numbers in the range from 0 to 3 expressed.

0 means less than 30% mortality

1 means 30 to 49% mortality

2 means 50 to 90% mortality

3 means more than 90% mortality.

For all pests the concentration of the compound according to the invention in the solutions used was 1000 parts per million (ppm); however, for Meloidogyne incognita (root node nematodes) the concentration used was 100 parts per million.

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link
No. black
sheet
louse green
sheet
louse £. uage red leaf
crazy
mite Table II white
Cabbage caterpillar Mustard-
Beetle House fly Root knot
tennema-
death • 1 Aphis
fabae Kegoura
viciae 3 Tetranychus
telarius chenosteri-
ler affect Pieris
brassicae Phaedon
cochleariae Kusca
aociestica Keloidogyne
incognita 2 broad bean 3 garden Tetranychus
telarius Cabbage Mustard/
paper Milk and
sugar
cotton water 3 I days 3 3 days Bean 3 days 2 days 1 day 2 days K 3 3 O 3 days O O 3 O 5 3 3 O O O 2 3 3 ro
CD O '
tr * vo 6th 3 3 O O O O O O CD
- <] UD ~
«T> I 7th 3 3 1 2 1 O 2 O 239 u> 8th 3 3 O O O O 3 O ^ *
IO 9 3 3 O 2 2 O "2 O 10 3 3 O O O 1 1 O 11 3 3 O O O O 2 O 12th 3 3 O O O O O O 3 1 2 O O O O 3 O O 2 2 O 2 3 O O O O O O O

Example 19

The activity of compounds according to the invention against mollusks was tested; Details of the carried out Tests are given below.

A weighed sample of the test compound in a small amount of an ethanol / acetone mixture (50:50 v / v) solved. The solution was on some bran in a glass petri dish poured; the solvents were allowed to evaporate. When the bran was dry it became a cooked 1.2% Agar-agar solution added to form a 4% solution of the active ingredient. The agar was allowed to settle and divided it among the repetitions. A plastic petri dish was provided for each repetition, the one Included bait, a snail, and some water to maintain a high relative humidity. The shells were left overnight; in a cold room (10 ° C).

The following morning the bait was removed and that Drained water. A filter paper disk was placed in the lid of each dish (all dishes were turned upside down Arrangement used) and moistened with fresh water. It became some {about 10) soaked wheat grains put in each bowl. Then the snails were wiaäar in the Brought to a cold room and left there for 7 days, adding extra food and water if necessary.

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After this time, death was determined.

This procedure was repeated for each chemical tested. There were 10 replicates for each test instead of.

The snails used were Agriolimax reticulatus (Müll.); they had starved for 24 hours before the tests began. The results of the tests are given in Table III below.

Table III Compound No. Slugs killed (%)

2 100 3 100 8th 100 Example 20

Preparations according to the invention were prepared in the following manner and tested in various ways with respect to various fungal diseases that occurred on leaves. The procedure chosen for each test is described below. \

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An aqueous solution or suspension containing 500 parts per million (ppm) of the test compound and suitable either for soaking the soil surrounding the growing plants or for spraying on shoots of cucumber, grapevine or apple seedlings was obtained by making water into a solution of 200 mg of the compound in ImI acetone was added until the total volume of the mixture was ² 100 ml. An aqueous solution or suspension, which was suitable for spraying onto the shoots of wheat, barley or rice seedlings, was prepared in the same way, but instead of water, a 0.1% (v / v) aqueous solution was used Solution of the polyoxyethylene sorbitan monolaurate additive "Tween" 20 is used ("Tween" is a symbol).

A. Protection test with spray application (P.S.A.)

A suspension or solution with a "

Content of 500 parts per million of active ingredient sprayed directly onto the shoots of plants, a wetting agent being used if the plants were wheat, barley or rice. After 24 hours, the plant was inoculated with the test fungus and after a suitable period of time (time interval A - see table below) the extent of the infection was determined visually, depending on the plant and the fungus.

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B. Protection test with soaking application (P.R.D.)

There was a suspension or solution containing 500 parts per million of active ingredient on the test plant surrounding soil and Ί8 hours later the plant was inoculated with the fungus. The extent of the Infection was determined visually after a period of time (time interval B - see table below) determined by the Plant and depended on the fungus.

C. Destruction test with spray application (E.S.A.)

The plants were inoculated with the test fungus, and 24 hours later the liquid mixture with a content of 500 parts per million of active ingredient was sprayed onto the plant shoots as described under A above. P After a further period of time (time interval C - see table below) - again depending on the plant and fungus - the extent of the infection was determined visually.

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Disease and plant

Time interval A and B (days)

Time interval C (days)

Puccinlh. 10 10 6th recondita J « 10 6th Phytophthora
infestana 7th 9 (Tomato) 7th Sphaerotheea
iuliginea 7th 7th 9 (Cucumber) *
7th Erysiphe
he amini s
(Wheat) - 21st Eryeiph. 8 i (barley) Pcdo3phaera
leucotricha !(Apple) Uncinula 20th necator l (V / a) Piasmopara
viticola (V / a) Piricularia oryzae
^r :( rice) Venturia ! inaequalis
( Apple )

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The results of the tests are given in Table IV below, with the extent of the disease as Is expressed grade, which reflects the extent of the disease in percent;

Required and extent of the disease (%)

0 61 to 100

1 26 to 60

2 6 to. 25 ■

3 0 to 5

U 0 9 8 3 6/2 2 5 0

Table IV

Connecting Pucoinia
rsconnita PRD > ESA Phytophthora
infestans PPJ) ESA Sphaerotheca PHD ESA G
S. BU) BSA 3rysiphe '
[. grarainls. PRD E3A, 0 dung υr. (Rust 0 0 (later
Fire) 2 - (Powder-
chimraal) 1 0 (Puiver-
sch imine 1 W 0 0 (Powder-
) schiitunelB]
j 0 0 PPE 0 0 0 - PPE 0 0 PPE 0 0 0 0 0 0 0 3 N> - 0 0 0 0 0 0 0 0 0 0 0 0 1 0 - 0 0 0 0 0 0 0 0 0 0 0 0 0 2 - 0 0 0 0 0 0 '0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 3 0 - 0 0 0 0 0 0 0 0 2 0 1 3 0 - 0 0 0 0 - « 0 «3» - 0 0 0 3 0 - 0 3 3 0 - - 0 - 3 0 0 0 3 0 - 0 - 3 3 3 - - - 0 1 0 0 0 - 3 3 3 3 - - - 0 0 3 3 3 1 0 3 _# - - 1 2 3 K 5 6th 7th 8th 9 • • 10 11 12th

wheat

barley

not tested

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Table IV (continued)

Podoaphaera
leuootrJiha. PRD E3A Unoinula
I nersator PRD ESL Pla.smopara
viticola PRD ESA Pirioularla
pryzae PRD ESA. Venturia
inaequalii PRL ESA I. - link
No. •(Powder-
is mold) O - (Powder
Mould) - - (Ripe
Mould) - (Meltau) 2 - (Pchorf) - - - FSi O PPE - - FSH - PPE. O - PS /. - - - 1 O O O - - O - - O O - - - - 2 O O - O - ' - O - - O O - - - - 3 1 O O - - O - - O O - - - 4th 1 O - O - - O - - O O - - - - 5 O O - O - - O - - O O - - - - 6th O O - 2 - - O - - O O - 3 - - 7th O - - O - - O - 1 O - - 1 8th O - - 1 - - O - - 1 O - - - 9 3 O - 3 - - 2 - - O O - 3 O 10 3 3 - 3 - - 3 - - O O - - - 11 3 1 O O 2 12th 3 - - O -

wheat

B = »barley

not tested

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Claims (1)

Claims 1. Pyrimidine compounds, their acid addition salts and pest control preparations containing them, characterized in that the pyrimidine compounds the formula / N own in the R ₁ and R _{2 are} lower alkyl groups, R ₁ - a hydrogen atom or a lower alkyl group is and in either (1) R, a hydrogen or halogen atom, a lower alkyl, alkenyl, benzyl or lower cyanoalkyx group and Rh is a hydrogen atom, a lower alkyl or phenyl group or (2) R ₃ UiIR. together a tri- or tetramethylembrückengruppe dart; to 11 j η. ο 'y a; u < / / '/ 1 ο 2. Pyrimidine compound of the formula 3. Pyrimidine compound of the formula ■ ⁰¹ K? jew » NSCH, Ί. Pyrimidine compound of the formula O CK N-C-O 009836/2250 ORK3INAL INSPECTED 5. Pyrimidine compound of the formula 6. Use of pyrimidine compounds or preparations according to one of the preceding claims for controlling suckling by applying them to the pests or their whereabouts. 009836 / 22B0