JPS62292769A - Novel pyrimidine derivatives, manufacture and use as insecticides and fungicides - Google Patents

Abstract

(57) [Abstract] 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 novel pyrimidine derivatives represented by formula I below, methods for their production and their use as pest control agents.

Pyrimidine derivatives with microbicidal properties are already known (see European Patent Application No. 159,613) and have the following formula! The novel pyrimidine derivative represented by: shows excellent fungicidal and insecticidal activity.

Therefore, the object of the present invention is the expression! a- (In the above formula, R1 and R are independently hydrogen; halogen; cyanoi (Ot-C8)-alkyl; (C1-ca)-
Ha0 Furkylp (Cs-O--Furkyl (This is nitro, cyano, (CI-04)-alkoxy, (Ol-
04) mono- or di-substituted by -alkylthio or -N(R7)(b,))
8)-cycloalkyl, which may be substituted by (Cs-0n)-alkyl; (Cz-04
)-alkenyl; (C meaning-a)-haloalkenyl i (
Cs-04)-alkynyl; (CS-C4)-haloalkynyl 1(CB-C6)-cycloalkenyl; group -N
(Rt) (R1); (C1-C5)-alkylthio; (CI-C8)-alkoxy; (al-a.)
-Haloalkoxy; (Cw-C8)-alkylsulfinyl; (Ct-CS)-alkylsulfonyl; phenyltc may be halogen, nitro, cyano,
(Ct-04)-alkyl, (Os-C8)-alkoxy, (CS5o4)-alkylthio or (C1-Ct
) - substituted by haloalkyl): or phenoxy (which is sometimes substituted with halogen,
(Ol-0a)-alkyl, (ct-04)-haloalkyl or (CI-04)-alkoxy); RsH hydrogen; halogen; cyano; nitro; (Ot-C8
)-alkyl; (Ct-(:!s)-haloalkyl;
(CS-C4)-alkenyl; (C1-C4)-haloalkenyl; phenyl (which may also include halogen, nitro, cyano, (C1-C4)-alkyl, (C1-C4)-alkyl;
I-04)-alkoxy, (c.

-C4)-alkylthio or (C1-04)-haloalkyl) or phenoxy(
In some cases, this is a halogen, 1aO! , (Ol-O
n)-alkyl, substituted by (ct-ca)-haloalkyl or (Cs-04)-alkoxy); R4'11 water IA; halogen; (C□-04)-alkoxy; (Os- Ca)-alkylthio: group N (
Rt) (Rs) or phenoxy (which may be substituted by halogen)'Ik;
Ct-Ca)-alkyl, (C1-C4-7/L/koxy)carbonyl, (C1-04-flukenyloxy)carbonyl, -Co! -can(R7) (Rs); (C1-C
4-Alkyl)carbonyl; (C1-C4-alkenyl)carbonyl; (Cs-C4-alkynyl)carbonyly (CS3- C'a-haloalkyl)carbonyl;
Os-Oa-haloalkynyl)carbonyl;Schiff/;=
l-1';B (0)nR,;S (0)nOR@
or 5(0)nN-(R7)(Rs); halogen i (Or-04)-no-roalkoxy; (Ol
-04) -Haloalkyl; means formyl; n means the number O11 or Fi2; R1 means 80 or CFB; R7 and the formula independently of each other are hydrogen; (C104)-
Alkyl; (Cs-07)-cycloalkyl (which may be substituted by (C1-Cm')-alkyl): phenyl (which is halogen, (Ol-0
4)-Alkyl, (C1-04)-haloalkyl, (C
s-CS4)-alkoxy; (C1""04)-alkylthio, nitro or cyano); letter R is (Os-0a)-alkyl; (CS-0a)
)-alkenyl; (Os-0a)-alkynyloxy(C,-C8)-cycloalkyl, which is (C1-C4
)-alkyl); R8° are independently hydrogen; (Ol-04)-alkyl; (CS-C8)-7chloroalkyl, which is
optionally substituted by l-C4)-alkyl)
; (Ct-04-alkoxy)carbonyl; (C
I-04-furkyl)carbonyl; (CSt-Ca)-
Alkoxy; phenyl (in some cases halogen, nitro, cyano, (Ct-04)-alkyl, (Ct
-Ca)-alkoxy% optionally substituted by (C1-C4)-alkylthio or (C-C8)-haloalkyl), and X is the group -NRI. -NR, o, -NRlo- or -〇-] Pyrimidine derivatives or salts thereof (wherein, X means the group -IJ Rlo- and Rs is OF,
Or an expression that means NO□! ).

Suitable salts are, in particular, the salts which can be used in practice, such as, for example, alkali metal salts, alkaline earth metal salts, ammonium salts or substituted ammonium salts. Salt formation occurs when the group X is -N Rlo- or -Ml. This is done when NH- or when R,=COO. Salts are prepared from compounds of formula 1 according to conventional methods.

Halogen means in particular fluorine, chlorine or bromine.

The prefix "halo" in the name of a substituent here and below means that this substituent may occur once or several times with the same or different meanings. The prefix halo means fluorine, fluorine, Chlorine, bromine and iodine, special fluorine, chlorine tit includes bromine. Examples of haloalkyl include: CI'll caIP,, 0HIF t 0C
1s* CjHO4+ 0H2(!t*○Brs,
cy=az, aczy,, CW20HF
g, C'F@CIP3゜OF, CHF0F,,
OF, 0HctF, OF, 0HO4=, cc
tl-004t n-03F7 p -○B(01
'3)1, n-04F*t n-C5-'1
1 s n-0@l'ts e n-C4 'll and "-Ca 'l 7.

Haloalkoxy sequences include: 001Fm, 001(F!, oaIP, oaF
l, 0OIF! 0HIPC! IF,.

ocy, cz, oaIP! cplcp,, o
aF, caFaz and OCF, OIF, (!IF, 0
IFs.

(Of-04)-Haloalkenyl PJ includes the following: Cj El -OF-p F! O-CF-;
C40-COl - Preferred compounds of formula (1) as defined above are those in formula I in which R1 is hydrogen; halogen; cyano; (OHC8)-alkyl; (C1-(!s)-haloalkyl; (C1-C
-)-Alkyl, which is (CtO*)-alkoxy or (o, -C4)-alkylthio, or disubstituted) i(Os-C8)-cycloalkyl, which is (C1-C4) - optionally substituted by alkyl); (]1-06)-fur#yfr; (
Ot-(3v)-a/I/ :2 xy; (OH-O
s) -furkylsulfinyl; ("1-C8)-furkylsulfonyl; phenyl, which is optionally mono-polysubstituted by halogen or
or nitro, cyano, (Or-C1)-alkyl, (
Ol-Oa)-alkoxy or (Ot-04)-
mono- or tri-substituted by haloalkyl), and R, is optionally substituted phenyl,
x, bx hydrogen; halogen; cyano; nitro; (Ct-O
s)-alkyl; (C1-C4)-haloalkyl if
c is phenoxy (this may be halogen, N
o! , (C1-ct)-alkyl, (Ol-04) -
R means hydrogen; halogen; or (CjL-04)-alkoxy; R, is (C1- C8)-alkyl, (C1-C4-al;oxy)carbonyl, -co! H; -cONcR7
)(R@) i (Ol-04-alkyl)carbonyl; (Cs-Ca-haloalkyl)carbonyl; cyano, halogen, nitro; also n 5(o)QN(R7)(
Rs)? : means i n means number 0.1i or 2; R@ means No! or CF; R7 and Rs are independently hydrogen i (C1-C4
)-alkyl; (Ol-07)-cycloalkyl, which may be substituted by (Ol-Cj4)-alkyl; or phenyl, which is halogen, (C1
-C4)-alkyl, (C1-C4)-haloalkyl'
! fcVi (CI-04) - which may be substituted with 7- or tri-substituted by flukoxy); R111 independently of each other is hydrogen; (CI-04) - means alkyl; and X is a group -NRIO- It is a compound meaning NRIO or -NRlo- or -0-.

Particularly preferred compounds for this purpose are compounds of formula (1) in which R, is (01-c8''> -haloalkyl, (C1-C
4)-Alkyl; (03-C.)-cycloalkyl, phenyl or phenyl, substituted as above,
in particular substituted by (C,-C8)-haloalkyl), R1 means Hi or (C1-C4)-alkyl, R1 means H or halogen, R4 means H or halogen means R@Ca(Ot-Ca-alkoxy)carbonyl, cyano"("l-c4) -/% O alkoxy, (C1
-04)-Haloalkyl maku means chlor, R@
represents NO2 and X represents NU or 10-.

The subject of the invention is also the formula! The above formula is characterized in that the compound represented by formula n is reacted with the compound represented by 2 in the presence of a base to produce the compound represented by ! This is a method for producing a compound represented by

Substituents R4%RhR1, R4, R@ and R6 are of formula I
has the same meaning as in. ■ and stomach are halogen, hydroxy, group -NR1°NHRl.

or the group -HFiR1@, in which case when W represents halogen, ■ is hydroxy, the group -NR1,
-NERt@ or the group -MER1, and if V represents halogen, W is hydroxy, the group -NR,. HHlo or group -NBRI
o must mean the radical R10 has the formula Irc
It has nine meanings. The term halogen stands for fluorine, chlorine, bromine and iodine, especially chlorine and bromine.

The reaction of compound 1 with 1 is preferably carried out using an inert aprotic solvent 1 such as acetonitrile, dichloromethane,
Toluene, xylene, tetrahydrofuran, dioxane, dialkyl ether, e.g. diethylene glycol
It is carried out in a dialkyl ether, such as a diethylene glycol-dialkyl ether, especially diethylene glycol diethyl ether, or DMIP at a temperature between -10 DEG C. and the boiling point of the solvent.

As bases, the usual bases for these types of reactions,
For example, alkali metal and alkaline earth carbonates and bicarbonates, alkali metal hydroxides, alkali metal alcoholates, potassium tert-butyrate, tertiary amines, pyridine-substituted pyridine bases (e.g. 4-dimethylamino pyridine) is preferred.

The second equivalent of the compound represented by the general formula (Aqui
valent) can also substitute for the function of a base.

In formula (2), V is a group -NRt. N R16 is a group -N
Only compounds of the formula (1) with HR10 are suitable as bases in this case.

The reaction is carried out at 0°C in aprotic solvents such as e.g. acetonitrile, diethylene glycol dimethyl ether, dichloromethane, toluene, tetrahydro7rane, dioxane or DMF, as well as in protic solvents such as methanol, ethanol or isopropanol. It is carried out in a temperature range of from to the boiling temperature of the solvent.

The second compound is basically synthesized by a known method [
For example, Journal of Organic Chemistry (J, Org, Chem, ) 26.

4504; U.S. Pat.
ender Organisohen Chemie
, Band 10/2, S.

252)]. Most of the compounds represented by 2) are known and can be easily obtained by conventional methods [for example, Liebigs Annaren der Hemi-366,
93(:C4iθbig's mna1an der
Chemie s6b, q3); British Patent No. 951
, No. 770; Chemical Abstracts (OA) 79,
78564x; CA 84, 30640k reference. Compound 2, where W is OH, is prepared from the corresponding compound in which hydrogen is present in place of the nitro group by a conventional nitration reaction. Compounds where W is halogen are
It is obtained by subsequent halogenation. Special compounds in which R is haloalkoxy and their preparation are described in German patent application P, 564 479 & 6 VC.

The compounds of formula I according to the invention are distinguished by a very good fungicidal action. Fungal pathogens that have already invaded the plant tissues are also effectively and curatively eradicated.

This is of particular importance and is advantageous in the case of fungal diseases which, once infected, can no longer be effectively eradicated by conventional fungicides. Range includes a number of different economic VCs
Important plant pathogenic fungi, such as Piric
ulariaoryzae), powdery mildew fungi, Fusarium spp.
Grape downy mildew fungus (Plagmopora viti)
aola) and downy mildew (Pseudop)
eronospora cubenaia) f. Strains of Botrytis cinerea susceptible to, and also resistant to, benzimidazoles and dicarboximides and strains of ECM susceptible and resistant Pseudocercosborella herbotricoides (pseuaocerc).
osporella herpotrichoides
) strain? Particularly effective extermination (DC!M=active substance Carbendazim) Formula a■
The compounds of the formula are also suitable for use in the industrial field, for example as wood protectants, in paints, as preservatives in cooling lubricants for metal processing or as preservatives in drilling and cutting oils.

The compounds of formula I, particularly those such as the examples below, may also be advantageously combined with other known fungicides.

As such combination ingredients, the following products are used: Imazalil (Xmagtsli1'), Prochloraz (Prochloraz), Fuenavani A/ (F
enapanil), 887105, Triculumizo-A
/ (Triflumizol), PP 969,
IQutriafol, EAR-MEE 6401, Propiconazol, Ktaconazol, Diclobutrazol, Eiter-Demorph (Tridemorph),
Dodemorph', Fenp-ropimorph, Falimorph, S-32165, Ohlo-benzthiacin
e), Parinol, Euthiobat, Fenpropidin, Triforin
fori-ne), Fenarimo A/ (Fenar
imol), Nuarimol,
Tr-1amol, Ethirimol, Dime
thirimol), Bupirim
ate), Ra'benz-A/ (Ra'benz
a-zole), tridicracy A/ (Tria
yclazole), offlace (0furaae)
), Fu-ralaxyl, Penalaxyl/l/ (Benalaxyl), Metalaxyl (Mθtalaxyl), Bendiuron (Pena
yuron), Oxadixy A/ (Oxadixy
1), Oyprofuram, nichlomezin, Probena-zols, Fluobenzimins.

Pyroxyfur, NK-48
3, PP-389, Pyroquilon
), Hymexazola, Fen1tropan, UEF-8
227, Dorclofosmeth A/ (To'lclofo
smethyl), Citalimphos (Ditalimf)
os), Edifenphoa
, Pyrazophoa, x, (Pyrazophoa).

Isobrothiolane
, cymoxanil, dichloruranid, captafo pv (C!api-tafOl), cabtan (c
aptan), Folpet),
? Tolyl-f'1uanid
, Chlorothaloni A/ (Chlorothalo-n1
1), Nitridiazo-A/ (1tridiazol
), iprodione (prodione), procymidone dithiano 7 (Dithianon'), dinocap (Dl-nocap), binapacuri A/ (Bi
napacryl), fentin acetate (Fen
tinaaetate)°, 7-entine hydroxide, carboxin, oxycarboxin (0X
7QarbOXin), Pyracarbolide (Pyra-
carbolid), metofloxam (Methfu
roxa8), Fenfuram
, Furmecycloz'
, Benodani'l, Mebenil, Mepro
-n11), 7A/Flutolanil, Fu'beridazole A/, Thiabendazole, Carpendazim (Oarbe=ndazim), Benomi A
/ (Benomyl), Thiophanate (Th1o
fanate), thiophanate-methy# (Th
iophanate-methyl), C0D-94
240F'.

Engineering KF-1216, Mancozeb, Mane
b), Nabam, Thira
m), Propineb, Pro-thioaarb, Propamocarb, Dodine
), Guazatine, Dialoran', Qut-n
tozene), chloroneb (ahloroneb)
), Tscnagene, biphenyl, anisidine, 2-phenylphenol, copper compounds such as Cu-oxychloride, oxine-Ou, Ou-oxide, sulfur, fosetylaluminum, sodium-dodecylbenzenesulfonate, sodium -dodecyl sulfate, sodium-〇ss/0ts-alcohol ether sulfonate, sodium-cetostearyl phosphate ester, dioctyl-sodium sulfosuccinate, sodium-isopropylnaphthalene sulfonate, sodium-methylene bisnaphthalene sulfonate, cetyl-trimethyl-ammonium chloride, Salts of long @ primary, secondary i 9 Vi tertiary amines, alkyl-propylene amines, lauryl-pyrimidinium bromide, ethoxylayered quaternized fatty amines, alkyl-dimethyl-benzyl-ammonium chlorides and 1-hydroxy Ethyl-2-alkyl-imidacyline.

The above active substances, indicated by their common names, are mostly listed in the Pesticide Handbook, edited by Worthing and Walker, 7th edition (1985) (C
B.R.Worthing, S.B.Walker
, The Pe5ticide Mannal ,
7th Hd, (1983).

Er1tish Crop Protection 0
). The compound indicated by the number code has the following structure: )1. OtO The bactericidal action of the active substance combination according to the invention is.

Unexpectedly in many cases the so-called Colby (Cjol)
by) is higher than the sum of the effects of the individual components calculated according to the formula (13,R, Go'lby, Weed
s Giant, 20-22 ('1957)), therefore,
The combination of these active substances shows a synergistic effect.

The weight ratios of the active substance groups in the active substance combinations vary over a relatively wide range. Generally, compounds of formula I 1
In terms of parts by weight, there are 5 to 10 parts by weight of the active substances of the combined components, preferably 2.5 to 1001 parts by weight.

The active substance combinations according to the invention have a strong microbicidal action and can therefore be used advantageously for the control of microorganisms, especially in plant storage.

The excellent tolerability of the active substances according to the invention to plants in the concentrations required for the control of plant diseases makes it possible to treat the above-ground parts of plants, the plants and seeds, as well as the soil.

The active substance combinations according to the invention have a very wide range of action and can be used against parasitic fungi that infest the above-ground parts of plants or attack Vi plants from the soil.

(Ustilago') % Septoria f14
(5eptoria'), Typhu If (Typhu
la), Rhynchosbo
rium), Hermisothosborium (Helmin
thosporium ) and Fusarium (F
It shows outstanding action as a seed soaking agent against plant pathogenic fungi such as P. uaarium ').

those of the genus Pythium (Pythiu8),
Verticillium,
Ph1alophora,
Also as a soil treatment agent for controlling plant pathogenic fungi that cause root rot and andromycosis, such as Rhlo-ctonia, Fusarium and Th1e'1aviopsis pathogens. used.

If the active substance combination according to the invention is applied directly to the above-ground parts of plants, a large number of economically important pathogens,
For example, powdery mildew fungi [Eryaiphe
), Unci-nula, Sphaerotheca, Podoaphaera, Leveillula taurica'
], Rust SaW, Benzulia, Cercospora, Alternaria, Botrytis, Phytophthora, Peronosvora, Piriculariaor
yzae) and sheath blight fungus (Pellicula
riasasaki) is very significantly divided by 5@.

The compound represented by formula 1 has excellent tolerability to plants and is toxic to warm-blooded animals @Ia, so it is not harmful to animal pests.
Particularly suitable for controlling insects, ridges and nematodes,
It is especially suitable for the control of insects which occur in the VC, Q industry, forestry, in the protection of stored goods and materials and in the field of hygiene. They are effective against normally susceptible and resistant genera and against all or individual growth stages. The pests VC mentioned above include the following: From the order of the Isopods (Opoda), for example, the water beetle (Oniscus asellu)
a), Armadi-111dium
vulgare), woodlouse (Forcell)
.

5caber).

From the order Diplopoda, for example, Blaniulus gut
tu'1atus) 11th labiopoda (0hlopoda)
) from Gsophi'lus
carpophaga), digi (8cutige-
ra BpθC4).

From Symphyla, for example, Scutigerslla immaculat.
a).

From the order Thyaanura', for example Lepisma 5accharina.

From the order Collembola (Collem'bola), for example Onyahiurus
armatus).

From the order of Orthoptera, for example, the Oriental cockroach (Elatta orient, aria),
American cockroach (Pariplaneta ameri)
cana), Leucophea maderae (Leucop)
haaa maderae), German cockroach (B
lattrla germanica), Gry-11 otalpa spp, Locustamigratoria
migratorioides), Melanoplus differencialis (Melanoplus diff)
Schistocerca gregaria), Schistocerca gregaria
.

From the order Dermaptera, for example, Forficula auricul.
aria).

From the order Termites, Reticulitermes app.
.

From the order of Lice, Phylloxera v.
astatri-X), Pemphigidae (Pemph
igus spp, ), Pedic
ulug humanua corporis), Haematopinua app, ),
Linognathus spp.
).

From the order Ma1'lophaga, e.g. Trichoaectea ap.
p, ), Damalina spp.
, ).

From the order of the order Thysanoptera, e.g.
notri-pa femora'1is), thrips (Thripa tabaci').

From the order Heteroptera, the order is Eiurygaater,
Gisderus Intermezius (Dyadercua)
intermediua), Pieama quadrata (Pieama quadrata), bedbug (Cimez 1ectularius), assassin bug (
Rhodnius prolizus), Tri-atomas (Tri-atomas), and Homoptera (Homoptera), including Aleurodes braasi
cae), Bemesia tabaki
aci), Tria V ourodes vavolariorum (T.
ria'1 eurodes vapor-rarioru
8), cotton aphid (Mphia goaaypii)
), radish aphid (Brevicoryne b.
raaaicae), Cryptomydus rivis (Ory
ptomyzus ribis), Doralia fabae (Doralia fabae), Doralia bomi (
Doralia pomi), apple bollworm (Rr
iosoma lanigeru8), peach aphid (Hyalopterua arundinia)
), Macrosiphum aphid
avenae), apple aphids (M7Zu8
Bpp, ”), hop aphid (Phor
odon humuli), wheat aphid (R
hopalosiphun padi), F. mpoaaca spp.
lobatus), leafhopper (Nephot)
ettix uncticeps), Lecanium corni, Cysetia oleae (8aisBettia olsae),
Lao-delphaz 5tria
tellua), brown planthopper (Nilapa)
rvata lugens), red scale insect (Aonliella aurantii), white scale insect (Aapidiotus hederae)
), Paeudococcus
app-), pheasant lambs (Psy-11a app-),
)0 From the order Lepidoptera, for example, the cotton aphid (Peotinophora gosaypi)
ella), Bupal A/S Vinialium (Bupal
us piniarius), Cheimatobia pumata (Cheimatobia 'brumata), Golden moth (Lithoaolletis blanca)
rdella), Hypono
meuta pade'la), diamondback moth (Plutel)
la maculipennia), Japanese plum beetle (Ma
lacosoma neustria), brown moth (Eu
proctischrys+orrhoea), gypsy moth (Lymantriaspp-'), and small moth (B
ucaulatrix thuberiella),
Phyllocniatrig c
itrrla), grotill 8
pp-), Euxoa spp.
, Heliothis spp., Heliothis spp. -Laphygma e:cigu
a), Armyworm (Mamestrabrassica)
e), Panolisflame
mea'), Prodenia 1i
tura), Spodoptera
spp, '), shear = (Tric
hoplusia ni), Carbokabusa bone bomanella (
Oarpocapsa pomonela), Pieris spp., chllo app., Pieris spp.
yraus-ta nubilalia), Epheatiakuahniella, Galleria melloneF
la), Cacoecia po -
dana), Capua Reteikrana (Oapua
reti-culana), Choristoneura fumifuerana (Ohoristoneura fumi)
ferana), Clysia 6ambiguera (C1ys
ia ambiguella), Chabamaki (Homo
na magnanima), Tortrix viridana.

From the order Co1. eoptera, for example, Anobium puncta
tu8), Risoberta Dominica (Rhizopert)
a dominiaa), Bruchidius obtectus (Bruchidius 0bts-atua), Bruchidius canthoacelid θ8C8
) tactus ), Hylotorbes Φbayurus - (1 (
ylot-rupea bajulua), Agelaatica alni, Leptinotars decemlineata (Leptinotars)
a aecemlineata), potato beetle (Phaed
on cochleariaa), Diabrochi dynamo (on cochleariaa),
Diabrotica spp, ), Paylli-odes chrysocephal
a), Epi-1achna var.
inetia), Atomariaap
p.)
surinamensis), weevils (An
thonomus spp-), Black elephants (81top
hilus spp, ), Otiorrhynchus eul-Catus
) s Cosmobolites sorgidius (Oosmop
Centhorrhynchus assimi, 1
1s), Eypera postica
), Dsrmes-tag app,
), Trogoderma s
pp, L Anthrenus (Anthrenus EIP)
8), ), Attagenus s
pp, '), Lyctusa jA (Lyctusa
pp, ), Meligethes Aeneus
esaeneus), Ptinus s
pp, ), Niptua h.
ololeucus), Gib
bium psylloidea), Tribolium 81), ), Tenebrio molito
r), Agriotes spp.
), Oonoaerus spp.
) %:llF Melontha
melolontha), Amphimallon solstiatialis
alis) and Costeritra zealandica (Co
θta-1ytra zealandica).

From the Hymenoptera (Hymenoptθra), for example, Kropodi 2, Diprion 8pp-
Hoplocampa spp., Laeius spp., Monomo-rium pharaon.
is) and Vespaspp - from the Diptera, gAJ, Aaaea spp., Ha'Ydaraka (
Anophelas spp,).

Culex (Oulex spp), Drosophila melanog
aster), house flies (Muaca sp.
p, ) 11 Fanniaapp-
), black fly (Calliphora erythro
cepha-'la), Luci'li
a spp, ), hryaomy
ia spp, ), Outerebr
a 8pp, ), Gastrophyllus (Gastrop)
hilus spp, ), and bobosca (Hyppo
-bosca spp, '), stable flies (stom
oxys spp, ), Oestrus
us 5l) p, ), Hypoderm
a spp, ), horseflies (Ta'banus spp.
, 1 Tannia spp., Eibi.

hortulanus), Oscinella fritto (Os
cine-11a fr4), Phorbia (Phor
bia spp, ), Peg.
omyia hyoecyarni), Ceratitis cavitata (Cθratitiθcapita-ta),
Citrus fly (Dacus olθizu and Kiryuji)
Tipula paluaosa).

From the order Chiliformes (81phonaptera), there are Xenopayl fleas (81phonaptera).
eopis) and Ceratophyllus (Ceratop
hyllus app, ).

From the order Murachnida, for example, Scorpio maurua,
Latrodectus mactans
maatans).

The subject of the present invention is therefore a pest control agent containing a compound of the formula I together with suitable formulation auxiliaries.
In particular, it shall mean fungi and pests, especially pests that attack plants.

The agent according to the present invention includes an irrigation agent, an emulsion, a spray solution, a powder,
It is used in the usual formulation forms as dipping agents, dispersants, granules or microgranules.

Wettable powders are preparations that can be dispersed homogeneously in water, which together with the active substances, diluents or in addition to inert substances, also wetting agents, such as polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, Alkyl-
or alkylphenol-sulfonate and dispersant, fMJ, sodium ligninsulfonate, 2.
Sodium 2'-sina7tylmethane-6'-disulfonate, sodium dibutylnaphthalene sulfonate, and sodium oleoylmethyltaurate. Their production takes place in the usual manner, for example by grinding and mixing the respective components.

Emulsions are prepared, for example, by dispersing the active substance in an organic solvent such as butanol, cyclohexanone, dimethylformamide, xylene or a high-boiling aromatic compound or hydrocarbon.
It can be prepared by dissolving with the addition of emulsifiers or more. In the case of liquid active substances, the solvent can be omitted completely or partially. As an emulsifier,
For example, the following may be used: calcium salts of neararylsulfonic acids, such as calcium dodecylbenzenesulfonate or nonionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide. Ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbit esters.

Dusts are obtained by grinding the active substance with finely divided solid substances, such as talc, naturally occurring clays, such as kaolin, bentonite, phyllite or diatomite.

Granules are prepared by spraying the active substance onto absorbent granular inert substances or by applying a concentrate of the active substance to binders such as sand, kaolinite, etc. using binders such as polyvinyl alcohol, sodium polyacrylate or mineral oil. can be prepared by coating on the surface of a solid carrier material or a granulated inert material. Suitable active substances can also be granulated, optionally mixed with the fertilizer, in the manner customary for the production of fertilizer granules.

In wettable powders, the active substance concentration of both active substances is
Approximately 10 to 90% by weight, with the balance up to 100% consisting of conventional pharmaceutical ingredients. In the case of emulsions, the active substance concentration of both active substances can be approximately 10 to 80% by weight. Powders usually contain 5 to 20% by weight of active substance, spray solutions approximately 1 to 20% by weight of active substance. In granules, the content of active substance is
Whether the active substance is a liquid or not in solid form and what granulation aids, fillers, etc. are used depends to some extent.

Furthermore, the active substance formulations described above optionally contain the respective customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, solvents, fillers or carrier substances.

For use, concentrates present in commercially available form are optionally diluted with water in the customary manner, for example as wetting agents, emulsions, dispersants and also in the case of microgranules. .

Powders and granules as well as spray solutions are no longer diluted further with inert substances before use.

The use of active substances of formula (1) can vary within a wide range and is generally from 0.010 to 5 to 9/ha.

The following columns explain the invention in more detail.

A. Formulation Examples Example: A powder is obtained by mixing 10 parts of active substance and 90 parts by weight of Merck as inert substance and milling in a hammer mill.

Example B: One hydrating agent that can be easily dispersed in water contains the active substance 2.
5 parts by weight, 64 parts by weight of kaolin-containing quartz as an inert material, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleoylmethyltaurate as a wetting and dispersing agent and by grinding in a bottle disc mill. can get.

Example C: A easily dispersible dispersion concentrate in one water contains 20 parts by weight of the active substance in an alkylphenol polyglycol ether (Triton X207) (S parts by weight, indridecanol polyglycol ether (Eo
8 units) and 71 parts by weight of paraffinic mineral oil (boiling range e.g. above about 255-377°C) and milling in a ball mill to a fineness of less than 5 microns.

11HID: One emulsion is obtained from 15 parts by weight of active substance, 75 parts by weight of cyclohexanone as solvent and oxyethylated nonylphenol (10 units of KO) as emulsifier.

B. Preparation sequence To a solution of 4.451 (1018 mol) of 5-chloro-2-trichloromethyl-4-pyrimidyl-amine in anhydrous zonitrile HF150 was added 5.152 (1018 mol) of KOH powder at -5°C.
1092 mol of C) was added.

Then a solution of 4.101 (1018 mol) of 4-chloro-5-dinitrobenzonitrile in 30% of anhydrous TEF was added.
The mixture was added dropwise so that the temperature did not exceed 0°C. After continued stirring for 5 hours, the solid components were separated by suction and the solvent was evaporated and concentrated under reduced pressure. The residue was taken up in water and acidified with dilute hydrochloric acid. It was then extracted with chloroform, dried over MgSO4, evaporated under reduced pressure and the solid obtained was recrystallized from diisopropyl ether.

Melting point = 214-215°C.

Figure 12.10 5-chloro-2-(i.

1.2.2-Tetrafluoroethyl)-4-pyrimidinyl-amine 9.143 t (α04 mol) in a solution of
44 sr (α08 mol) of KOH powder was added at -5°C. After that, anhydrous T) IF10〇-Medium ethyl 4
-chloro-5-dinitro-benzo-! --) IC
l38 f ([104 mol) + 2) solution.

The mixture was added dropwise so that the temperature did not exceed 0°C. 3 at 0℃
Stirring was continued for an hour and the reaction mixture was then allowed to warm to room temperature for 2 hours. The solid components were then removed with suction and the mother liquor was concentrated by evaporation.

The solid residue was recrystallized from ethyl acetate.

Melting point: 257-260°C.

Column 526 2CO3:L3 in 50d of acetonitrile? followed by 4-chloro-5-dinitro-pencitrifluoride 4.5 y (α16 moA/) and 5-
A solution of 58 t (α16 mol) (2) g of methyl-2-perfluoroethyl-4-pyrimidinol was added dropwise. The mixture was heated to reflux If for 3 hours, the precipitate was filtered off with suction and the solution was evaporated under reduced pressure. The residue was recrystallized from diisopropyl ether. Melting point: 90-92
℃.

Column 167 To a solution of 4-chloro-5-dinitro-pencitrifluoride 2.7f (cL0 1 mol) in ethanol 80-, FLfc5-)f-2 dissolved in ethanol 30-
-berfluoroethyl-4-pyrimidinylhydrazine t
a4r (α02 moles) was added within 30 minutes. It was then boiled at reflux temperature for 5 hours, and then the solvent was evaporated under reduced pressure. The residue was taken into water and extracted with chloroform.

The organic phase was dried over t-Na1804 and evaporated under reduced pressure. The precipitated solid material was recrystallized from diisopropyl ether. Melting point: 135-137°C Example & 16 In a solution of 4-chloro-3,5-dinitro-pencitrifluoride')-7tC101 mol) in ethanol, N-methyl-N-(6-
Methyl-2-trichloromethyl-4-pyrimidinyl)-
Hydrazine S1? (51 L02 mol) was added dropwise over 30 minutes. The mixture was boiled at reflux temperature for 5 hours, then evaporated to dryness, the residue was dissolved in chloroform, washed with water, dried over Na1804 and evaporated under reduced pressure. The precipitated solid material was recrystallized from diisopropyl ether. , @ point: 160-163°C.

Similarly to Example 1, the compounds of Table 1 were prepared, as in Example 2, the compounds of Table 2 were prepared, as in Column 3, the compounds of Table 3 were prepared, and as in Column 4, the compounds of Table 4 were prepared. and the same as column 5 and 11:1 to produce the compounds in Table 5.

C1 biological test example 1. Bactericidal action example 1 Using the compound according to the present invention (Table 1)
jlJ'X sotL(" tL 200 o〉rmni 2
's 00 ;-ppm was added to biomalt agar. After the agar had set, it was inoculated with 61 different strains of the fungus that were sensitive to and resistant to benzimidazole and Iprodion. 20μ of the spore suspension was applied to the center of the agar plate.

Samples were evaluated 6 days after inoculation. The effect of the active substance is expressed as a percentage compared to the control (agar medium without active substance).

Example 2 The compounds according to the invention (Table 2) were added to biomalt agar at concentrations of 50 and 8 ppm of active substance '1j125, respectively.

After the agar solidifies, Pseudoselfosporella culture (
Pseudoceraoaporella ) (B
CM-susceptible and BGM-resistant) were inoculated.

20μ of the spore suspension was applied to the center of the agar plate. Samples were evaluated 6 days after inoculation. The effect of the active substance is
It is expressed as a percentage compared to the control (agar medium without active substance).

Table 2a 4.190 100
100 80 Control O 2nd BCM-susceptible strain BCM-resistant Shuzono strain control
0 Example 3 Mliler-Thurga4' which is susceptible to downy mildew (Plaamopara)
) j'! The grape seedlings obtained from the young trees of i were
At the leaf stage, the treatment was carried out with an aqueous suspension of the compound according to the invention in which droplets drop 1. The concentration used was 500.250 and 1251.
It was v.

After the spray film dries, the plants become infected with downy mildew (P'las).
The suspension was inoculated with a suspension of zoosporangia of C. mopara viticola) and kept at a constant temperature of about 20 DEG C. and a relative air humidity of about 100 DEG C. in dripping wet conditions. After 24 hours, the infected plants were removed from the thermostatic chamber and grown in a greenhouse maintained at a temperature of about 23° C. and an air humidity of about 8° to 9° C.

After a 7-day culture period, plants were placed in a constant chamber and diseased. Next, we evaluated JK level. The degree of vine infestation is expressed as the percentage of affected leaf area compared to infected but untreated control plants and is listed in Table 3.

Table 3 tsa a a a
2.50 0 0 01.
190 0 0 01.48
0 0 01.179
0 0 01.213
0 0 01.8
0 0 01.46
0 0
01.214 0 0 0
1.643 0 0 01.
192 0 0 01.92
0 0 01.251
(] 0 01.250
0 0 01.49
0 0
04.93・0 0
02.77 0 0
04.98 0 0 0
100 Untreated Infected Plants Example 4 Apple seedlings (EMIX) were treated at the four-leaf stage with the compound according to the invention at 500 doses of active substance per liter of spray solution.
．． Uniform treatments were carried out at working concentrations of 250 and 125η.

After the liquid film of the active substance has dried, the above-mentioned seedlings are strongly inoculated with conidia of the apple scab fungus (Vanturia 1naequaliθ) and grown under moist conditions at about 22°C and about It was placed in a constant temperature room maintained at 100% relative air humidity. After a 48 hour infection period, the ifs were placed in a greenhouse maintained at approximately 18°C and a relative air humidity of 95-100°C.

After a 14-day incubation period, the seedlings were infected with V.
nturia inaθqualis) was examined. The evaluation of the degree of tension was done visually as if passing by. The infestation of plants by sclerosis is expressed as a percentage of the leaf area affected relative to infected but untreated plants and is reported in Table 4.

According to the side numbers below in Table 4, the prevalence of scabies at the concentration of the active substance η compound below per spray liquid 1 (A) 1.209 0
0 01.213
0 0 0
Example 5 Wheat seedlings were heavily inoculated with conidia of wheat powdery mildew M (Eryeiphe graminea) at the three-leaf stage and placed in a greenhouse maintained at 20°C and 90-95% relative air humidity. On the day of contact,
These seedlings were treated with the compounds and active substances listed in Table 5. After a 10 day incubation period, the plants were examined for infestation of wheat powdery mildew. Infestation is expressed as a percentage of the leaf area affected with reference to infected but untreated control plants (=100% infestation). The results are summarized in Table 5.

Table 5 2.77 0 0 0L201
0 0 0 Untreated infected plants 100 Example 6 Cucumber seedlings [Delikatess]
] was infected with cucumber powdery mildew fungus (E
ryaiphe cichoracearum)
was heavily inoculated with a suspension of conidia. After allowing the spore suspension to dry for 30 minutes, the seedlings were kept in a greenhouse at 22° C. and 90% relative air humidity.

38 days after inoculation, the seedlings were treated with the compounds and active substance concentrations described in Section 6.

Plants were evaluated after 10 days. Infestation is expressed as a percentage of the area of nine infected leaves relative to infected but untreated control plants (~100 vines). The results are summarized in Table 6.

Table 6 1.201 0
0 0 Untreated infected plants
100 Examples of Synergistic Effects Using Examples of IprOdiOn Cross-Strip Test in Veto IJ Dishes [Journal.
Op General Microbiology (J, Gen
, MicrobioL 126 (1981).

(method described in pp-1-7)) The synergistic relationship between the active substances of Akisou is the so-called crossover)
It can be determined in vitro by the IJ tube test.

A strip of r paper (width 10 m, length 90 pieces) was prepared using formula I
Compound and combination component represented by (Iprodione)
A suspension culture of the microorganisms to be tested (approximately 200 µt/strip) was uniformly wetted using a formulation of
15 sd (approximately 10" to 10 conidia/1-) are first added onto the still liquid state agar in each Petri dish. Each Petri dish contains one representative example of a compound of formula l. A strip of f-paper is placed containing the iprodione, and at right angles thereto is placed a second strip containing the combined component (iprodione). By routine experiments, their concentrations are selected to correspond to the so-called minimum inhibitory concentration for the microorganisms tested.

Approximately 6 lbs.
After incubation for up to 4 days, the diameter of the zone of inhibition in the area of the crossed test strips is measured and evaluated as an indicator of synergistic effect.

Seventh table chiasm strip test Test target: Botrytis cine
rea) b) 250 0 Iprodione c) 500
8 (Iproaion) d)
250 0 combination of active substances arc 500+500 16add
500 + 250 84.117
+4 progeo 7 b+c 250+50
0 1O-12baa 250 +
250 62 Insecticidal action example 8 Tetranys urticae,
Severely infested French bean (Phasθ〇−
1ug v, ) was sprayed with an aqueous dilution of the emulsion containing 100 ppm of the specific active substance.

The killing rate of ticks was checked after 7 days. 100% kill rate is
Example 1.643:1.200:1.251:1.471:
This was achieved by using compounds according to t481 and 1.291.

Example 9 A young apple tree (Malus commu) heavily infested with apple spider mite (Panonychus ulmi).
nie) was treated as in Example 1.

After 8 days, the killing rate of ticks was measured. The killing rate of ioo% is
Example 1.92: Achieved by using compounds according to 1.200 and 1,481.

Example 10 Bean aphid (Aphis craccivora)
) was severely infested with Japanese lentils (Vicia fab).
a) was sprayed with an aqueous dilution of an irrigation agent having an active substance content of 1.000 ppm until the [1111] was easily removed.

The killing rate of aphids was measured after 3 days.

and 1.471.

Example 11 Whitefly (Trialeurodes vapora)
Bean trees heavily infested with P. rioru 8) were sprayed with an aqueous suspension of a hydrating powder concentrate (active substance content 1,000 ppm) until 9 drops began to fall easily.

When the above plants were examined under a microscope 14 days after being placed in the greenhouse, a 100% killing rate was found in Example 2.51.2.
．． 50. Results of 9 were obtained when using formulations containing 1.189 and 1,200 compounds.

Thousand chestnuts 12 11 ft of each of the formulations to be tested were applied as an emulsion in water evenly to the inside of the lid and bottom of the Petri dish, and after the coating had dried, 10 house flies (
Muscad Omes-tica) was added.

After closing the Petri dishes, they were kept at room temperature and the killing rate of experimental animals was determined after 6 hours. 1.000pp
At a concentration of m (based on the content of active substance),
Preparation 1.255, 1.2, 1.256, 1.8°1.
298, 1.214, 1.643, 1.192゜1.9
2, 1.442, 1.140, 1.267° 1.268
, 1.200, 1.201, 1.222° 1.223.
1.197. 1.215. 1.10°1.58,
1.4, 1.159. 528, 1.251°1.1
, 1.250, 1.101, 1.291° 1.471.
1470. 1.481 and t 284 are 100
% killing rate.

Example 13 Place 10 Blatella cockroaches in each Petri dish treated as in Example 12.
germanica) larvae (L4), close these dishes, and reduce the kill rate of these experimental animals to 5.
I got it checked a day later. At a concentration of 1,000 ppm (based on the content of active substance), the preparation 1.194. 1
．． 125°t256. 1B, 1.298. 1.
645°1, a 42. t20 o, 1.22
2. 1.4°1.139. 1.251. 1.28
4 and 1.2 showed 100% kill rate.

Claims (1)

[Claims] 1. Formula I ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (I) (In the above formula, R_1 and R_2 independently represent hydrogen; halogen;
Cyano; (C_1-C_2)-alkyl; (C_1-C
_8)-haloalkyl; (C_1-C_8)-alkyl {this can be nitro, cyano, (C_1-C_4)-alkoxy, (C_1-C_4)-alkylthio or -N(
R_7) mono- or di-substituted by (R_8)}; (C_3-C_8)-cycloalkyl, which may be substituted by (C_1-C_4)-alkyl; (C_2-C_4), - Alkenyl; (C_
2-C_4)-haloalkenyl; (C_3-C_4)-
Alkynyl; (C_3-C_4)-haloalkynyl; (
C_5-C_6)-cycloalkenyl; group -N(R_7
)(R_8);(C_1-C_8)-alkylthio;(
C_1-C_6)-alkoxy; (C_1-C_8)-
Haloalkoxy; (C_1-C_8)-alkylsulfinyl; (C_1-C_8)-alkylsulfonyl; phenyl {which may optionally be halogen, nitro, cyano, (C_1-C_4)-alkyl, (C_1-C_4)-
alkoxy, substituted by (C_1-C_4)-alkylthio or (C_1-C_4)-haloalkyl}; or phenoxy {which may optionally be halogen, NO_2, (C_1-C_4)
-alkyl, (C_1-C_4)-haloalkyl or substituted by (C_1-C_4)-alkoxy}; R_3 is hydrogen, halogen, cyano, nitro, (C_1-
C_8)-alkyl, (C_1-C_8)-haloalkyl, (C_2-C_4)-alkenyl, (C_2-C_
4) -Haloalkenyl, phenyl {which may also include halogen, nitro, cyano, (C_1-C_4)-alkyl, (C_1-C_4
)-alkoxy, (C_1-C_4)-alkylthio or (C_1-C_4)-haloalkyl} or phenoxy {which is optionally substituted by halogen, NO_2, (C_1-C_4
)-alkyl, (C_1-C_4)-haloalkyl or (C_1-C_4)-alkoxy}; R__4 is hydrogen, halogen, (C_1-C_4)-alkoxy, (C_1-C_4)-alkylthio , group N(R
_7) (R_8) or phenoxy (which may be substituted by halogen); R_5 is (C_1-C_4)-alkyl, (C_1-C
_8-alkoxy)carbonyl, (C_1-C_4-alkenyloxy)carbonyl, -CO_2H, (C_2
-C_4-alkynyloxy)carbonyl; (C_1-
C_4-haloalkoxy)carbonyl; (C_2-C_
4-Haloalkenyloxy)carbonyl; (C_2-C
_4-Haloalkynyloxy)carbonyl; -CON(
R_7) (R_8); (C_1-C_4-alkyl)carbonyl; (C_2-C_4-alkenyl)carbonyl; (C_2-C_4-alkynyl)carbonyl; (C_
2-C_4-haloalkyl)carbonyl; (C_2-C
_4-haloalkenyl) carbonyl, (C_2-C_4
-haloalkynyl)carbonyl;S(O)_nR_9;
S(O)_nOR_9 or S(O)_nN(R_7)
(R_8); Halogen, cyano, nitro; (C_1-C
_4)-haloalkoxy; (C_1-C_4)-haloalkyl; means formyl; n means the number 0, 1 or 2; R_6 means NO_2 or CF_3; R_7 and R_8 independently of each other hydrogen, (C_1-C_4)-
alkyl; (C_3-C_7)-cycloalkyl, which may be substituted by (C_1-C_4)-alkyl; or phenyl {which is halogen, (C_1-C_4)-alkyl,
(C_1-C_4)-haloalkyl, (C_1-C_4
)-alkoxy; (C_1-C_4)-alkylthio,
optionally substituted by nitro or cyano}; R_9 is (C_1-C_4)-alkyl; (C_2-C
_4)-alkenyl, (C_2-C_4)-alkynyl or (C_3-C_7)-cycloalkyl, which is (
C_1-C_4) - optionally substituted by alkyl); R_1_0 are each independently hydrogen; (C_1-C_4)
-alkyl; (C_3-C_7)-cycloalkyl, which may be substituted by (C_1-C_4)-alkyl; (C_1-C_4-alkoxy)carbonyl, (C_1-C_4-alkyl)carbonyl; (C
_1-C_4)-alkoxy; phenyl {this may be halogen, nitro, cyano, (C_1-C_4)
)-alkyl, (C_1-C_4)-alkoxy, (C
_1-C_4)-alkylthio or (C_1-C_4
)-haloalkyl}, and X is a group -NR_1_0-NR_1_0, -NR_1_0
- or -O-] or a salt thereof, where X is a group -
Excludes compounds of formula I in which NR_1_0- is meant and R_5 is CF_3 or NO_2. 2. In formula I, R_1 is hydrogen; halogen; cyano; (C_1-C_8)
-alkyl; (C_1-C_8)-haloalkyl; (C
_1-C_8)-alkyl (this is (C_1-C_4)
-alkoxy or (C_1-C_4)-alkylthio); (C_2-C_8)-cycloalkyl, which is (
C_1-C_4)-alkyl); (C_1-C_8)-alkylthio; (C_1
-C_8)-alkoxy; (C_1-C_8)-alkylsulfinyl; (C_1-C_8)-alkylsulfonyl; phenyl, which is optionally mono- or polysubstituted by halogen and/or nitro, cyano, (C_1 -C_4)-alkyl, (C_1-C
_4)-alkoxy or (C_1-C_4)-haloalkyl), and R_2 is optionally substituted phenyl
1, and R_3 is hydrogen; halogen; cyano; nitro; (C_1-
C_8)-alkyl; (C_1-C_8)-haloalkyl or phenoxy {which may optionally be halogen, NO_2, (C_1-C_4)-alkyl, (C_1-C_4)-haloalkyl or
R_4 is hydrogen; halogen; or (C_1-C_4)-
means alkoxy; R_5 is (C_1-C_4)-alkyl, (C_1-C
_4-alkoxy)carbonyl, -CO_2H; -CO
N(R_7)(R_8); (C_1-C_4-alkyl)carbonyl; (C_3-C_4-haloalkyl)carbonyl; cyano, halogen, nitro; or S(O)_nN(R_7)(R_8); n is means the number 0, 1 or 2; R_6 means NO_2 or CF_3; R_7 and R_8 independently of each other are hydrogen; (C_1-C_4)-
alkyl; (C_3-C_7)-cycloalkyl, which may be substituted by (C_1-C_4)-alkyl; or phenyl {which is halogen, (C_1-C_4)-alkyl,
(C_1-C_4)-haloalkyl or (C_1-C
_4) - which may be mono- or tri-substituted by alkoxy}; R_1_0 are independently hydrogen; (C_1-C_4)
- means alkyl; and X is a group -NR_1_0-NR_1_0 or -NR_1
_0 or -O-) Compounds represented by formula I according to claim 1 and salts thereof. 3. In formula I, R_1 is (C_1-C_8)-haloalkyl, (C_1
-C_4)-alkyl; means (C_3-C_6)-cycloalkyl, phenyl or phenyl, which is substituted as above, in particular by (C_1-C_8)-haloalkyl, in which R_2 is H or (C_1 -C_4)-alkyl, R_3 means H or halogen, R_4 means H or halogen, R_5 is (C_1-C_4-alkoxy)carbonyl,
Cyano; (C_1-C_4)-haloalkoxy, (C_
1-C_4)-haloalkyl or chlor, R_6 means NO_2 and X means NH or -O-, and their salts. 4.Formula I ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the above formula, R_1 and R_2 are independently hydrogen; halogen;
Cyano; (C_1-C_8)-alkyl; (C_1-C
_8)-haloalkyl; (C_1-C_8)-alkyl {this can be nitro, cyano, (C_1-C_4)-alkoxy, (C_1-C_4)-alkylthio or -N(
R_7) mono- or di-substituted by (R_8)}; (C_3-C_8)-cycloalkyl, which may be substituted by (C_1-C_4)-alkyl; (C_3-C_4)-alkenyl ;(C_2
-C_4)-haloalkenyl; (C_3-C_4)-alkynyl; (C_3-C_4)-haloalkynyl;
_5-C_6)-cycloalkenyl; group -N(R_7)
(R_8); (C_1-C_8)-alkylthio; (C
(C_1-C_8)-alkoxy; (C_1-C_8)-haloalkoxy; (C_1-C_8)-alkylsulfinyl; (C_1-C_8)-alkylsulfonyl; C_4)-alkyl, (C_1-C_4)-
alkoxy, substituted by (C_1-C_4)-alkylthio or (C_1-C_4)-haloalkyl}; or phenoxy {which may optionally be halogen, NO_2, (C_1-C_4)
-alkyl, (C_1-C_4)-haloalkyl or (C_1-C_4)-alkoxy}; R_3 is hydrogen, halogen, cyano, nitro, (C_1
-C_8)-alkyl, (C_1-C_8)-haloalkyl, (C_2-C_4)-alkenyl, (C_2-C
_4) -Haloalkenyl, phenyl {which may also include halogen, nitro, cyano, (C_1-C_4)-alkyl, (C_1-C_4)
)-alkoxy, (C_1-C_4)-alkylthio or (C_1-C_4)-haloalkyl} or phenoxy {which is optionally substituted by halogen, NO_2, (C_1-C_4
)-alkyl, (C_1-C_4)-haloalkyl or (C_1-C_4)-alkoxy}; R__4 is hydrogen, halogen, (C_1-C_4)-alkoxy, (C_1-C_4)-alkylthio , group N(R
_7) (R_8) or phenoxy (which may be substituted by halogen); R_5 is (C_1-C_4)-alkyl, (C_1-C
_8-alkoxy)carbonyl, (C_1-C_4-alkenyloxy)carbonyl, -CO_2H, (C_3
-C_4-alkynyloxy)carbonyl; (C_1-
C_4-haloalkyl)carbonyl; (C_2-C_4
-haloalkenyloxy)carbonyl; (C_3-C_
4-Haloalkynyloxy)carbonyl; -CON(R
_7) (R_8); (C_1-C_4-alkyl)carbonyl; (C_2-C_4-alkenyl)carbonyl;
(C_3-C_4-alkynyl)carbonyl; (C_3
-C_4-haloalkyl)carbonyl; (C_2-C_
4-haloalkenyl)carbonyl, (C_3-C_4-
haloalkynyl)carbonyl;S(O)_nR_9;S
(O)_nOR_9 or S(O)_nN(R_7)(
R_8); Halogen, cyano, nitro; (C_1-C_
4) -Haloalkoxy; (C_1-C_4)-haloalkyl; means formyl; n means the number 0, 1 or 2; R_6 means NO_2 or CF_3; R_7 and R_8 independently of each other hydrogen, (C_1-C_4)-
alkyl; (C_3-C_7)-cycloalkyl, which may be substituted by (C_1-C_4)-alkyl; or phenyl {which is halogen, (C_1-C_4)-alkyl,
(C_1-C_4)-haloalkyl, (C_1-C_4)-alkoxy; optionally substituted by (C_1-C_4)-alkylthio, nitro or cyano}; R_9 is (C_1-C_4)-alkyl; ( C_2-C
_4)-alkenyl, (C_2-C_4)-alkynyl or (C_3-C_7)-cycloalkyl, which is (
C_1-C_4) - optionally substituted by alkyl); R_1_0 are each independently hydrogen; (C_1-C_4)
-alkyl; (C_3-C_7)-cycloalkyl, which may be substituted by (C_1-C_4)-alkyl; (C_1-C_4-alkoxy)carbonyl, (C_1-C_4-alkyl)carbonyl; (C
_1-C_4)-alkoxy; phenyl {this may be halogen, nitro, cyano, (C_1-C_4)
)-alkyl, (C_1-C_4)-alkoxy, (C
_1-C_4)-alkylthio or (C_1-C_4
)-haloalkyl}, and X is a group -NR_1_0NR_1_0, -NR_1_0-
or -O-] In order to produce a compound represented by the formula or a salt thereof,
The compound represented by II is expressed by formula III.
0NH_2 or -NHR_1_0, in which case W
represents halogen, V is hydroxy, group -NR
_1_0-NHR_1_0 or the group -NHR_1_0 and when V represents halogen W is hydroxy, the group -NR_1_0NHR_1_0
or the group -NHR_1_0)
A method for producing a compound represented by the above formula I or a salt thereof, which comprises reacting the compound represented by the formula I in the presence of a base, and optionally converting the obtained compound into a salt thereof. 5.Formula I ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the above formula, R_1 and R_2 are independently hydrogen; halogen;
Cyano; (C_1-C_8)-alkyl; (C_1-C
_8)-haloalkyl; (C_1-C_8)-alkyl {this can be nitro, cyano, (C_1-C_4)-alkoxy, (C_1-C_4)-alkylthio or -N(
R_7) mono- or di-substituted by (R_8)}; (C_3-C_8)-cycloalkyl, which may be substituted by (C_1-C_4)-alkyl; (C_2-C_4)-alkenyl ;(C_2
-C_4)-haloalkenyl; (C_3-C_4)-alkynyl; (C_3-C_4)-haloalkynyl;
_5-C_6)-cycloalkenyl; group -N(R_7)
(R_8); (C_1-C_8)-alkylthio; (C
(C_1-C_8)-alkoxy; (C_1-C_8)-haloalkoxy; (C_1-C_8)-alkylsulfinyl; (C_1-C_8)-alkylsulfonyl; C_4)-alkyl, (C_1-C_4)-
alkoxy, substituted by (C_1-C_4)-alkylthio or (C_1-C_4)-haloalkyl}; or phenoxy {which may optionally be halogen, NO_2, (C_1-C_4)
-alkyl, (C_1-C_4)-haloalkyl or (C_1-C_4)-alkoxy}; R_3 is hydrogen, halogen, cyano, nitro, (C_1-
C_8)-alkyl, (C_1-C_8)-haloalkyl, (C_2-C_4)-alkenyl, (C_2-C_
4) -Haloalkenyl, phenyl {which may also include halogen, nitro, cyano, (C_1-C_4)-alkyl, (C_1-C_4
)-alkoxy, (C_1-C_4)-alkylthio or (C_1-C_4)-haloalkyl} or phenoxy {which is optionally substituted by halogen, NO_2, (C_1-C_4
)-alkyl, (C_1-C_4)-haloalkyl or (C_1-C_4)-alkoxy}; R_4 is hydrogen, halogen, (C_1-C_4)-alkoxy, (C_1-C_4)-alkylthio , group N(R_
7) (R_8) or phenoxy (which may be substituted by halogen); R_5 is (C_1-C_4)-alkyl, (C_1-C
_8-alkoxy)carbonyl, (C_1-C_4-alkenyloxy)carbonyl, -CO_2H, (C_3
-C_4-alkynyloxy)carbonyl; (C_1-
C_4-haloalkoxy)carbonyl; (C_3-C_
4-Haloalkenyloxy)carbonyl; (C_3-C
_4-Haloalkynyloxy)carbonyl; -CON(
R_7) (R_8); (C_1-C_4-alkyl)carbonyl; (C_2-C_4-alkenyl)carbonyl; (C_3-C_4-alkynyl)carbonyl; (C_
3-C_4-haloalkyl)carbonyl; (C_2-C
_4-haloalkenyl) carbonyl, (C_3-C_4
-haloalkynyl)carbonyl;S(O)_nR_9;
S(O)_nOR_9 or S(O)_nN(R_7)
(R_8); Halogen, cyano, nitro; (C_1-C
_4)-haloalkoxy; (C_1-C_4)-haloalkyl; means formyl; n means the number 0, 1 or 2; R_6 means NO_2 or CF_3; R_7 and R_8 independently of each other hydrogen, (C_1-C_4)-
alkyl; (C_3-C_7)-cycloalkyl, which may be substituted by (C_1-C_4)-alkyl; or phenyl {which is halogen, (C_1-C_4)-alkyl,
(C_1-C_4)-haloalkyl, (C_1-C_4
)-alkoxy; (C_1-C_4)-alkylthio,
optionally substituted by nitro or cyano}; R_9 is (C_1-C_4)-alkyl; (C_2-C
_4)-alkenyl, (C_2-C_4)-alkynyl or (C_3-C_7)-cycloalkyl, which is (
C_1-C_4) - optionally substituted by alkyl); R_1_0 are each independently hydrogen; (C_1-C_4)
-alkyl; (C_3-C_7)-cycloalkyl, which may be substituted by (C_1-C_4)-alkyl; (C_1-C_4-alkoxy)carbonyl, (C_1-C_4-alkyl)carbonyl; (C
_1-C_4)-alkoxy; phenyl {this may be halogen, nitro, cyano, (C_1-C_4)
)-alkyl, (C_1-C_4)-alkoxy, (C
_1-C_4)-alkylthio or (C_1-C_4
)-haloalkyl}, and X is a group -NR_1_0-NR_1_0, -NR_1_0
- or -O-] A pest control agent characterized by containing an effective amount of a compound represented by the following or a salt thereof, together with a suitable formulation aid. 6. The pest control agent according to claim 5, wherein an effective amount of the compound represented by formula I or a salt thereof is applied to animal pests, plants infested with them, or cultivation ground. 7.Formula I ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the above formula, R_1 and R_2 are independently hydrogen; halogen;
Cyano; (C_1-C_8)-alkyl; (C_1-C
_8)-haloalkyl; (C_1-C_8)-alkyl {this can be nitro, cyano, (C_1-C_4)-alkoxy, (C_1-C_4)-alkylthio or -N(
R_7) mono- or di-substituted by (R_8)}; (C_3-C_8)-cycloalkyl, which may be substituted by (C_1-C_4)-alkyl; (C_2-C_4)-alkenyl ;(C_2
-C_4)-haloalkenyl; (C_3-C_4)-alkynyl; (C_3-C_4)-haloalkynyl;
_5-C_6)-cycloalkenyl; group -N(R_7)
(R_8); (C_1-C_8)-alkylthio; (C
(C_1-C_8)-alkoxy; (C_1-C_8)-haloalkoxy; (C_1-C_8)-alkylsulfinyl; (C_1-C_8)-alkylsulfonyl; C_4)-alkyl, (C_1-C_4)-
alkoxy, substituted by (C_1-C_4)-alkylthio or (C_1-C_4)-haloalkyl}; or phenoxy {which may optionally be halogen, NO_2, (C_1-C_4)
-alkyl, (C_1-C_4)-haloalkyl or (C_1-C_4)-alkoxy}; R_3 is hydrogen, halogen, cyano, nitro, (C_1-
C_8)-alkyl, (C_1-C_8)-haloalkyl, (C_2-C_4)-alkenyl, (C_2-C_
4) -Haloalkenyl, phenyl {which may also include halogen, nitro, cyano, (C_1-C_4)-alkyl, (C_1-C_4
)-alkoxy, (C_1-C_4)-alkylthio or (C_1-C_4)-haloalkyl} or phenoxy {which is optionally substituted by halogen, NO_2, (C_1-C_4
)-alkyl, (C_1-C_4)-haloalkyl or (C_1-C_4)-alkoxy}; R_4 is hydrogen, halogen, (C_1-C_4)-alkoxy, (C_1-C_4)-alkylthio , group N(R_
7) (R_8) or phenoxy (which may be substituted by halogen); R_5 is (C_1-C_4)-alkyl, (C_1-C
_8-alkoxy)carbonyl, (C_1-C_4-alkenyloxy)carbonyl, -CO_2H, (C_3
-C_4-alkynyloxy)carbonyl; (C_1-
C_4-haloalkoxy)carbonyl; (C_3-C_
4-Haloalkenyloxy)carbonyl; (C_3-C
_4-Haloalkynyloxy)carbonyl; -CON(
R_7) (R_8); (C_1-C_4-alkyl)carbonyl; (C_2-C_4-alkenyl)carbonyl; (C_3-C_4-alkynyl)carbonyl; (C_
3-C_4-haloalkyl)carbonyl; (C_2-C
_4-haloalkenyl) carbonyl, (C_3-C_4
-haloalkynyl)carbonyl;S(O)_nR_9;
S(O)_nOR_9 or S(O)_nN(R_7)
(R_8); Halogen, cyano, nitro; (C_1-C
_4)-Haloalkoxy; (C_1-C)-haloalkyl; means formyl; n means the number 0, 1 or 2; R_6 means NO_2 or CF_3; R_7 and R_8 independently of each other hydrogen, (C_1-C_4)-
alkyl; (C_3-C_7)-cycloalkyl, which may be substituted by (C_1-C_4)-alkyl; or phenyl {which is halogen, (C_1-C_4)-alkyl,
(C_1-C_4)-haloalkyl, (C_1-C_4
)-alkoxy; (C_1-C_4)-alkylthio,
optionally substituted by nitro or cyano}; R_9 is (C_1-C_4)-alkyl; (C_2-C
_4)-alkenyl, (C_2-C_4)-alkynyl or (C_3-C_7)-cycloalkyl, which is (
C_1-C_4) - optionally substituted by alkyl); R_1_0 are each independently hydrogen; (C_1-C_4)
-alkyl; (C_3-C_7)-cycloalkyl, which may be substituted by (C_1-C_4)-alkyl; (C_1-C_4-alkoxy)carbonyl, (C_1-C_4-alkyl)carbonyl; (C
_1-C_4)-alkoxy; phenyl {this may be halogen, nitro, cyano, (C_1-C_4)
)-alkyl, (C_1-C_4)-alkoxy, (C
_1-C_4)-alkylthio or (C_1-C_4
)-haloalkyl}, and X is a group -NR_1_0-NR_1_0, -NR_1_0
- or -O-] A fungicide characterized by containing an effective amount of a compound represented by the following formula or a salt thereof together with a suitable formulation aid. 8. The fungicide according to claim 7, wherein an effective amount of the compound represented by formula I or a salt thereof is applied to harmful fungi, plants infested with them, or cultivation ground.