CY1247A - N-acylamino-2-oxo-3-oxazolidine derivatives and their use as fungicides - Google Patents

N-acylamino-2-oxo-3-oxazolidine derivatives and their use as fungicides Download PDF

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Publication number
CY1247A
CY1247A CY1247A CY124780A CY1247A CY 1247 A CY1247 A CY 1247A CY 1247 A CY1247 A CY 1247A CY 124780 A CY124780 A CY 124780A CY 1247 A CY1247 A CY 1247A
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Cyprus
Prior art keywords
compound
component
ch2och3
furyl
formula
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CY1247A
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Sandoz Ltd
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/18—Oxygen atoms
    • C07D263/20—Oxygen atoms attached in position 2
    • C07D263/26—Oxygen atoms attached in position 2 with hetero atoms or acyl radicals directly attached to the ring nitrogen atom

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Description

t
GB 2 058 059 A
1
SPECIFICATION Fungicides
5 The present invention provides compounds useful in the com bating of phytopathogenic fungi. More specifically the present invention provides compounds of formula I,
10 \ / 10
K
2
R3 \ *5 R6
R? 4
15 wherein Rt is 15
R/Hs
20 wherein R7 and R8, independently, are C^alkyl, halogen or C^ alkoxy, and Rg is hydrogen, Ci.4 alkyl or 20 halogen, R2 is CO-R10,
wherein R10 is C-i.4 alkoxy-C-M alkyl, C-|.4 alkylthio-C-^alky], 2-furyl, 2-tetrahydrofuryl, halogenated 2-furyl, halogenated 2-tetrahydrofuryl, 1-imidazolylmethyl, 1-pyrrazolyl methyl, 2-tetrahydrofuryloxymethyl, 2-tetrahydropyranyloxymethyl, or C^halogenalkyl, and
25 R3, R4, R5 and R6 are independently hydrogen or Ci_4alkyl. 25
When any of R3, R4, Rs, Re, R7, Rs or R9 is or includes an alkyl group (e.g. alkoxy), this is preferably C-1.3 alkyl, i.e. methyl, ethyl, n-propyl or/-propyl.
When either of R7 or R8 is halogen, this is F, CI, Br of I, preferably F, CI or Br, more preferably CI or Br,
particularly CI.
30 When any of R9or R10is or includes halogen this is F, CI, Br or I, preferably F, CI or Br, particularly CI or Br. 30
Preferred halogenated 2-furyl significances of R10 are monohalogenated 2-furyl, e.g. 5-chloro-2-furyl and 5-bromo-2-furyl.
Preferred Cv4 halogenalkyl significances of R10 are C^chloroalkyl, or Ci.4bromoalkyl, e.g. chloromethyl, bromomethyl and C2H5 CHBr-;
35 Preferred halogenated 2-tetrahydrofuryl significances of R10 are monohalogenated 2-tetrahydrofuryl, 35
particularly monochlorinated or monobrominated 2-tetrahydrofury! e.g. 5-chloro-2-tetrahydrofuryl.
Preferred C^alkoxy-C^alkyl significances of R10 are C^alkoxymethyl, particularly CH3OCH2- and C2H5OCH2-.
Preferred Ci.^alkylthio-CT-^alkyl significances of R10 are Cvsalkylthiomethyl, e.g. CH3SCH2-;
40 R10 is preferably C^alkoxy-C^alkyl, 2-furyl or 5-halo-2-furyl. 40
When one of R3 and R4 is Ci_4alkyl, the other is preferably hydrogen.
When one of R5 and Rg is Ci.4alkyl, the other is preferably hydrogen.
Thus, a preferred group of compounds are the compounds of formula la,
45 f1 A. 45
la
50 50
wherein R2' is -COCH2OCH3, -COCH2OC2H5, -CO-(2-furyl) or -CO-(5-halo-2-furyl), R?' and R8' independently : are CH3, CI or Br and R9' is H, CI, Br or methyl whereby R7' and Ra' are preferably identical.
According to a further aspect of the present invention, the compounds of formula I are produced by intramolecular condensation of a compound of formula II 55 55
o rc r,. r, r.
h .. 5n / 6 4 yr - c - o - c c - y ii
R1 - N\
C " R10
60 0 60
wherein R1f R3, R4, R5, R6 and R10 are as defined above and Y is halogen.
Y is preferably chlorine or bromine, particularly chlorine.
The above intramolecular condensation can be carried out in a conventional manner. The reaction is 65 exothermic. It can e.g. be carried out in a water free medium using as solvent an ether such as 65
BNSDOCID: <GB 2058059A__I_>
2 GB 2 058 059 A
2
dimethoxyethane, an hydrocarbon such as toluene or an other solvent which is inert under the reaction conditions. The reaction temperature is not critical and can lie between about 0° and 100°C. Since the reaction is exothermic one starts the reaction conveniently at room temperature and allows the reaction temperature to rise gradually.
5 The reaction is conveniently carried out in the presence of an acid binding agent such as sodium hydride, 5 sodium amide or a sodium alcoholate e.g. sodium ethylate.
The intramolecular condensation can also be carried out in an aqueous/organic two-phase system in the presence of an anorganic base e.g. sodium hydroxide and optionally a catalytic amount of a phase transfer catalyst. The organic phase may comprise any appropriate inert water immiscible solvent such as ■
10 hydrocarbons or halogenated carbons, e.g. xylene, toluene, o-dichloro benzene or dichloromethane. 10
Appropriate phase transfer catalysts are quaternary ammonium compounds such as benzyltrimethyl ammonium bromide, quaternary phosphonium compounds such as benzyltriphenyl phosphonium chloride and crown ethers such as 18-crown-6.
The compounds of formula II are novel. They may be obtained by acylation of compounds of formula ill 15 15
r± - nh - nh - c - 0 c c y iii
20 wherein R1, R3, R4, R5, R6 and Y are as defined above, with a compound of formula IV, 20
O
R10 - C - Z IV
25 25
wherein R10 is as defined above, and Z is halogen, particularly CI, or O-COR10,
wherein R10 is as defined above.
Suitable solvents for this acylation reaction are hydrocarbons such as toluene or halogenated 30 hydrocarbons such aschlorobenzene.The reaction is conveniently effected ata temperature of from about 30 50° to about 120°C, e.g. 80=C.
The compounds of formula III may be obtained by conversion of compounds of formula V,
R1-NH-NH2 V
35 35
wherein Ra is as defined above,
with a compound of formula VI
.. 5\/ 6 3\ / 4
40 x - c - o c c v vi 40
wherein R3, R4, R5, R6 and Y are as defined above, and X is halogen, particularly CI.
This conversion may be effected at a temperature of from about 0C to about 10CC in water or in an organic 45 solvent which is inert under the reaction conditions, conveniently in the presence of a base e.g. an organic 45 amine or sodium hydrogen carbonate.
The starting materials and reagents employed in the processes described above are either known or,
insofar as they are not known, they may be produced in analogous manner to the processes described herein or to known processes.
50 The compounds of formula I have useful fungicidal activity, particularly against phytopathogenic fungi, 50 especially against fungi of the class Oomycetes as indicated by a significant effect in the following tests.
Test A : Fungicidal effect against Phytophthora infestans Young potted potato plants {3-5 leaf stage) are sprayed with an aqueous spray suspension containing 55 0.003% (weight volume) of a compound of formula I, e.g. 2-methoxy-N-(2,6-dimethylphenyl)-N-(2-oxo-3- 55
oxazolidinyD-acetamide (formulated in accordance with Formulation Example I). Two hours later, the treated plants are inoculated with a spore suspension of Phytophthora infestans and the plants are then transferred to a tent providing 100% relative atmospheric humidity at an ambient temperature of 16^ and a day length of 16 hours. Disease control is evaluated 4-5 days later by comparing the treated plants with untreated, 60 similarly inoculated plants. With the above test compound, substantial control of the fungal infestation is 60 observed without any sign of phytotoxivity on the host plants.
TestB : Fungicidal effect against P/asmopara viticola Young potted plants of grape vine (3-6 leaf stage) are sprayed with an aqueous spray suspension 65 containing 0.0008% (weight'volume) of a compound of formula I, e.g. 2-methoxy-N-(2,6-dimethylphenyl)-N- 65
BNSDOCID: <GB 2058059A_I_>
3
GB 2 058 059 A
3
(2-oxo-3-oxazolidinyl)-acetamide (formulated in accordance with Formulation Example 1). Two hours later, the treated plants are inoculated with a spore suspension of Plasmopara viticoia and the plants are then transferred to a tent providing 100% relative atmospheric humidity at an ambient temperature of 15 -22°C (fluctuating over a 24hr-period) and a day length of 16 hours. Disease control is evaluated 6 days after 5 inoculation by comparing the treated plants with untreated, similarly inoculated plants. With the test . compound, substantial control of the fungal infection is observed without any sign of phytotoxicity on the host plants.
. TestC : Curative fungicidal effect against Plasmopara viticoia
10 Young potted plants of grape vine (3-6 leaf stage) are inoculated in the same way as determined in Test B, but the application of the compound, e.g. 2-methoxy-IM-(2,6-dimethylphenyl)-N-(2-oxo-3-oxazolidinyl)-acetamide (formulated in accordance with Example I), follows only after 3 days after inoculation; the incubation conditions are the same as described in Test B. Disease control is evaluated as stated in Test B. With the test compound, substantial control of the fungal infection is observed.
15
Test D : Eradicative fungicidal effect against Plasmopara viticoia
The procedure to evaluate this kind of activity is evaluated as described in Test C, with the exception that the treatment is carred out only 6 days after inoculation, when sporulation on the lower leaf surface is alreay evident. Disease control evaluated 7 days after application of, e.g., 0.012% of compound 2-methoxy-N-(2,6-20 dimethylphenyl)-N-(2-oxo-3-oxazolidinyl)-acetamide {formulated in accordance with Formulation
Example 1), reveals a stopping effect on already sporulating zones, in that sporulation ceases completely.
Test E : Translocation in treated leaves of grape vines Excised leaves of grape vine are treated with an aqueous spray suspension containing 0.012% of 25 compound of formula I, e.g. 2-methoxy-N-(2,6-dimethylphenyl)-N-(2-oxo-3-oxazolidinyl)-acetamide (formulated in accordance with Formulation Example I), in that only the lower half of such leaves is treated. Two hours after treatment, the whole leaf is inoculated with a spore suspension of Plasmopara viticoia after which the leaves are incubated in a tent providing 100% atmospheric humidity at conditions as described in Test B. Although only the lower half of the leaves was treated as stated above, with the test compound 30 substantial disease control on the entire leaf inoculated was observed. The same effect was observed, when only the upper half of the leaves was treated. This Test thus shows, that the 2-methoxy-N-{2,6-dimethylphenyl)-N-(oxo-3-oxazolidinyl)-acetamide (formulated in accordance with Formulation Example I), is distributed within a leaf both acropetally and basipetally.
35 TestF : Soil treatment
In vico, employing Pythium aphanidermatum. The fungus is cultivated in a sterile mixture of sand and corn meal (97:3 v v) to which water is added in a ratio of about 1:4{v v); cultivation lasts for 4 days at 25~C. The fungus is then mixed into a semi-sterile mixture of peat and sand which then is treated with a suspension containing the formulated active ingredient to give concentration of 10 to 160 ppm (e.g. 10, 40 and 160 ppm) 40 calculated per volume substrate). The substrate is transferred to pots of 5 cm diameter which are seeded with cucumber seeds. The planted pots are incubated at 24°C and 60 - 70% relative humidity in an incubation chamber for 7 days, after which disease attack is determined by comparing the number of healthy emerged plants with that in untreated, similarly inoculated check pots. The compound of Example 1, hereinafter, used in the wettable powder formulation given above provides full disease control.
45 Tests analogous to Test F give similar results with peas and sugar beets.
Each of the compounds listed below in the following Examples is found to possess fungicidal properties indicating their usefulness as fungicides.
Particularly effective fungicidal activity is found in the above test with the compounds of formula la
• wherein R2' is COCH2OC2H5, R7' and Rs' are CH3 and R9' is H,
50 wherein R2' is CO-(2-furyl), R/ and R8' are CH3 and Rg'is H,
wherein R2' is CO-(5-bromo-2-furyl), R/ and R8' are CH3 and Ra' is H,
• wherein R2' is COCH2OCH3, R/ R8' are CI and R9' is H,
wherein R2' is COCH2OCH3, R7' and Ra' are CH3 and R9' is 3-Br and especially with the compound of formula la, wherein R2' is C0CH20CH3, R7' and R8' are CH3 and R9' is H. 55 The invention therefore also provides a method of combating phytopathogenic fungi, especially of the class Oomycetes, in plants, seeds or soil, which process comprises treating the plants, seeds or soil with a fungicidally effective amount of a compound of formula I.
Fungi of the class Oomycetes, against which the method of the invention is particularly effective, are those of the genus Phytophthora in plants such as potatoes, tomatoes, tobacco, citrus, cacao, rubber, apples, 60 strawberries, vegetables and ornamentals, e.g. Phytophthora infestans in potatoes and tomatoes; of the genus Plasmopara viticoia in grape vines; of the genus Peronospora in plants such as tobacco, e.g. Peronospora tabacina in tobacco; of the genus Pseudoperonospora in plants such as hops and cucumber, e.g. Pseudoperonospora humuli in hops; of the genus Bremia in plants such as lettuce, e.g. Bremia lactucae in lettuce; of the genus Pythium causing damping-off and root rots in a great number of plants, such as 65 vegetables, sugar beets, ornamentals and conifers, e.g. Pythium aphanidermatum in sugar beets; of the
BNSDOCID: <GB 2058059A_I_>
5
10
15
20
25
30
35
40
45
50
55
60
65
4
GB 2 058 059 A
4
genus Sc/erospora in plants such as sorghum and corn, e.g. Sclerospora sorghis in sorghum.
For use in the method of the invention, the amount of the preparation to be employed will vary depending on such factors as the species of fungi to be combated, the time and nature of application and the amount and nature of the compound of formula I employed in the preparation.
5 However, in general satisfactory results are obtained when applied to a locus, e.g. on crops orto soil with a dosage rate in the range of from 0.05 to 5 kg, preferably from 0.1 to 3 kg of a compound of formula l/ha treated locus, the application being repeated as required. When employed as a seed dressing, satisfactory results are obtained when applied at a rate of from about 0.05 to 05, preferably about 0.1 to 0.3 g compound of formula l/kg seed.
10 According to a preferred method of the invention the compounds of formula I are used in association with other fungicides which are effective against phytopathogenic fungi. Such combinations having an enhanced or broadened fungicidal activity.
A particularly preferred method of the invention comprises applying to the locus to be treated fungicidally effective amounts of 15 a component a) comprising a compound of formula I and of a com ponent b) selected from a component b1) a copper fungicide or a component b2) captan orfolpetor a component b3) mancozeb or maneb.
20 Examples of copper fungicides suitable for use as component b1)are copper (li) carbonate, copper (II) calcium sulphate, copper (II) carbon oxychloride, tetracupric oxychloride, Bordeaux mixture. Burgundy mixture, cuprous oxide, cupric hydroxide, copper (II) oxychloride or also copper complexes such as copper triethanolamine hydroxide of the formula [Cu N(CH2CH2OH)3 ]-(OH)2, commercially available under the Trademark K-Lox, or bis(ethyienediamine)-copper (II) sulphate of the formula [Cu(H2NCH2CH2lMH2)2]S04, 25 commercially available under the Trademark Komeen, and mixtures thereof, particularly cuprous oxide, " copper (II) oxychloride, cupric hydroxide and a mixture of copper (II) calcium sulphate and copper (II) oxychloride.
Captan, Folpet, Mancozeb and Maneb are the common names for protective fungicides effective against foliage diseases (Pesticide Manual, 5th Ed., by H. Martin and C.R. Worthing, page 76,281,328 and 329 resp.). 30 The method of this invention wherein component a) and component b) are used, is effective against a wide range of phytopathogenic fungi.
Preferably component a) is applied ata rate of 100-400 g/ha and component b) ata rate of 200-2000 g/ha.
Preferably the weight ratio of component a): component b) is in the range of 1:1 to 1:10, more preferably of 1:2 to 1:10, particularly of 1:2 to 1:7.
35 The method of the invention wherein component a) and component b) are used is particularly effective against phytopathogenic fungi in plants such as potato, tomato and other Solanaceae tobacco, citrus, cacao, rubber, apple, strawberry, vegetables and ornamentals, e.g. against fungi of the genus Plasmopara, e.g. Plasmopara viticoia in grape vine, of the genus Guignardia, e.g. Guignaridia bidwelli in grape vine of the genus Phoma in grape vine, of the genus Pseudopeziza, e.g. Pseudopeziza tracheiphila in grape vine, of the 40 genus Gloeosporium, e.g. Gloeosporium ampelophagum in grape vine of the genus Botrytis in grape vine and lettuce, e.g. Botrytis cinerea in grape vine, of the genus Phytophthora, Phytophthora infestans in potato, tomato or other Solanaceae, Phytophthora parasitica in tomato or other Solanacease, Phytophthora cryptogaea in tomato and other Solanaceae, Phytophthora mexicana in tomato and other Solanaceae, Phytophthora nicotianae in tobacco and Phytophthora palmivora in rubber or cacao, of the genus 45 Peronospora, e.g. Peronospora tabacina in tobacco, of the genus Pseudoperonospora, e.g. Pseudoperonos-pora humuti'm hop, of the genus Bremia in plants such as lettuce, e.g. Bremia lactucae, of the genus Pythium, e.g. Pythium aphanidermatum in sugar beet, of the genus Alternaria, e.g. Alternaria solani in potato, tomato and other Solanaceae, Alternaria tenuis in tobacco, of the genus Spondylocladium, e.g. Spondylocladium atrovirens in potato, of the genus Rhizoctonia. e.g. Rhizoctonia solani in potato, tomato 50 and other Solanaceae, of the genus Ciadosporium, e.g. Cladosporium fuivum in tomato or other Solanaceae, of the genus Colletotrichum in plants such as cacao or tomato, e.g. Colletotrichum atramentarium in tomato or other Solanaceae, of the genus Glomeralia, e.g. Glomerella lycopersici in tomato and other Solanaceae, of Corticium spp in tomato and other Solanaceae, of the genus Botryodiplodia, e.g. Botryodiplodia theobromae in cacao. This method of the invention allows the control of a significantly wider range of fungal diseases 55 than by treatment with only one of the components.
In general, a greater than additive effect of the components is observed, especially after treatment with concentrations of component a) and component b) allowing a practically complete, more specifically more than 80%, control of the fungi, particularly when copper (II) oxychloride, cuprous oxide, captan, mancozeb or maneb is used as component b), and especially when used against phytopathogenic fungi of the class 60 Oomycetes, especially against Oomycetes of the genus Phytophthora, e.g. Phytophthora infestans, of the genus Plasmopora, e.g. Plasmopora viticoia, of the genus Peronospora, e.g. Peronospora tabaccina, of the genus Pseudoperonospora, e.g. Pseudoperonospora humuli, of the genus Bremia, e.g. Bremia lactucae, and of the genus Pythium, e.g. Pythium aphanidermatum.
The method of the invention wherein the components a) and b) are used, is especially indicated for 65 combating or preventing fungi in grapevines, tomato and other Solanaceae and in cacao when a component
: <GB 2058059A L>
5
10
15
20
25
30
35
40
45
50
55
60
65
5
GB 2 058 059 A 5
b1) is used, in grapevines when a component b2) is used and in grape vines, potato, tomato and other Solanaceae, tobacco and hop when a component b3) is used.
The components a) and b) may be employed in formulation form and applied e.g. as a tank mix or separately. They are, however, preferably applied in admixture in the form of an aqueous spray or oil based
5 concentrate. 5
The useful fungicidal activity obtained after treatment with a component a) and b) is illustrated by the following tests.
! Test G : Fungicidal effect against Phytophthora infestans
10 The test is carried out as described in Test A, whereby the plants are treated with a tank mix of an aqueous 10 spray suspension containing component a) and component b) in concentrations indicated in Tables Ai to As below. The disease control is evaluated 4-5 days later by comparing the resuls with the effect that would be obtained if only an additive effect would arise. A more than additive effect is indicated, as illustrated in the following Tables A, to A6.
TABLE A1 TABLE A2
Component a) of Component a) of
Example 1 hereinafter (in ppm)
Example 1 hereinafter (in ppm)
0
2
8
32
E
0
2
8
32
E a
0
0
30
70
90
Q.
a c
0
0
40
80
100
a c
2
0
40 (30)
80 (80)
100 (100)
<1)
2
0
50 (40)
100
(80)
100 (100)
CD
*o
X
o
(A
3
8
20
60 (45)
90 (90)
100 (90)
X
o >
s:
CO
8
30
80 (60)
100 (85)
100 (100)
o u. Q. 3 a
32
60
80 (70)
100 (90)
100 (95)
O
i—
a D o
32
75
90 (85)
100 (95)
100 (100)
( ) calculated additive effect
(1) in commercially available Copper-Sandoz form
(2) in commercially available Kocide 101 form
BNSDOCID.' <GB_
_2058059A_I_>
GB 2 058 059 A
TABLE A3
TABLE A4
Component a) of Example 1 hereinafter (in ppm)
Component a) of Example 1 hereinafter (in ppm)
0
2
8
32
0
2
8
32
0
0
30
80
100
0
0
40
80
100
2
20
50
100
100
*p
2
30
70
90
100
E
Q.
(45)
(85)
(100)
a
(40)
(80)
(100)
Q.
c
C
8
40
80
100
100
8
20
90
100
100
s—
LU Q_
(60)
(90)
(100)
(50)
(85)
(100)
—I
O
Ll_
32
70
90
100
100
0L <
0
32
80
100
100
100
(80)
(95)
(100)
(90)
(95)
(100)
{ ) calculated additive effect.
TABLE A5 Component a) of
E
Q. Q. C
N
o o c
TABLE As Component a) of
Example 1 hereinafter (in ppm)
Example 1 hereinafter (in ppm)
0
2
8
32
0
2
8
32
0 0
20
80
95
0
0
30
70
95
2 20
80 (35)
100 (85)
100 (95)
E
Q.
2
30
70 (50)
90 (80)
100 (100)
8 40
90 (50)
100 (90)
100 (100)
Q.
.£
_Q <D
c
8
40
85 (60)
100 (80)
100 (100)
32 75
95 (80)
100 (95)
100
(100)
to
2
32
85
1.00 (90)
100 (95)
100 (100)
{ ) calculated additive effect.
BNSDOCID: <GB 2058059A_I_>
7
GB 2 058 059 A
7
Test H : Fungicidal effect against Plasmopara viticoia
The Test is carried out as described in Test B, whereby the plants are treated with a tank mix of an aqueous spray suspension containing component a) and component b) in concentrations indicated in Tables Bi to B6 below. The observed effect is given by the following Tables B, to B6. 5. 5
TABLE B, TABLE B2
10 10
Component a) of Component a) of
Example 1 hereinafter Example 1 hereinafter
(in ppm) (in ppm)
15
0
2
8
32
a
Q.
0
2
8
32
E a ry
0
0
30
70
100
CN
0
0
40
70
100
20
u.
_c aj
■o 'x
O »
2
10
30 (35)
70 (75)
100 (100)
0) ■D X o u-
T>
2
20
40 (45)
70 (75)
100 (100)
8
50
60 (65)
100 (85)
100 (100)
>
XL
01
D O
8
40
60 (60)
100 (80)
100 (100)
25
3 O
i—
a.
3 O
32
80
85
(85)
100 (95)
100 (100)
Q. 3
o
32
70
80 (80)
100 (90)
100 (100)
15
20
25
30 ( ) calculated additive effect 30
(1) in commercially available Copper-Sandoz form
(2) in commercially available Kocide 101 form
: <GB 2058059A l_>
GB 2 058 059 A
TABLE B3 TABLE B4
Component a) of Component a) of
Example 1 hereinafter Example 1 hereinafter
(in ppm) (in ppm)
10 10
?
Q.
Q.
15 j§ (80) (95) (100) < (80) (90) (100) 15
UJ
a.
_i
O u.
20 20
( ) calculated additive effect.
0
2
8
32
0
2
8
32
0
0
40
80
100
0
0
40
70
100
2
40
60
100
100
E
2
0
40
80
100
(65)
(90)
(100)
Q. Q.
f
(40)
(70)
(100)
8
70
80
100
100
z
8
70
95
100
100
(80)
(95)
(100)
<
H n
(80)
(90)
(100)
32
100
100
100
100
< CJ
32
100
100
100
100
(100)
(100)
(100)
(100)
(100)
(100)
25 25
TABLE Bs TABLE B6
30
35
E
Q. O. _C
.Q
40 ®
^ N
o o c
Component a) of Component a) of
Example 1 hereinafter Example 1 hereinafter
(in ppm)
(in ppm)
0
2
8
32
0
2
8
32
0
0
35
80
100
0
0
40
80
100
2
20
50
90
100
2
20
60
100
100
(50)
(85)
(100)
(50)
(85)
(100)
E
CL
Q.
8
60
90
100
100
8
70
95
100
100
c
(75)
(90)
(100)
(80)
(95)
(100)
_Q
<13
C CO
32
95
100
100
100
32
90
100
100
100
2
(100)
(100)
(100)
(95)
(100)
(100)
45
30
35
40
45
( ) calculated additive effect.
BNSDOCID: <GB 2058059A_I_>
9
GB 2 058 059 A
9
Thecompounds of formula I are conveniently employed as fungicidal compositions in association with agriculturally acceptable carriers or diluents. Such compositions also form part of the present invention.
They may contain aside from a compound of formula I as active agent, other active agents, such as fungicides, particularly a fungicide selected from the group comprised by component b) as defined 5 hereinbefore. They may be employed in either solid or liquid application forms e.g. in the form of a wettable 5 powder, an emulsion concentrate, a water dispersible suspension concentrate ("flowable"}, a dusting powder, a granulate, a delayed release form, incorporating conventional carriers, diluents and/or adjuvants.
Such compositions may be produced in conventional manner.
The compositions of the invention comprising both components a) and b) may for example be obtained by 10 mixing said components a) and b), optionally with a carrierand otherformulating ingredients. 10
Particularly formulations to be applied in spraying forms such as water dispersible concentrates or wettable powders may contain surfactants such as wetting and dispersing agents, e.g. the condensation product of formaldehyde with naphthalene sulphonate, an alkylarylsulphonate, a lignin sulphonate, a fatty alkyl sulphate, an ethoxylated alkylphenol and an ethoxylated fatty alcohol.
15 In general, the formulations include from 0.01 to 90% by weight of active agent, said active agent 15
consisting either of at least one compound of formula I or mixtures thereof with other active agents, such as fungicides e.g. a component b) as defined hereinbefore. Concentrate forms of composition generally contain between about 2 and 80%, preferably between about 5 and 70% by weight of active agent. Liquid application forms of formulation may contain from 0.01 to 20% by weight, preferably from 0.01 to 5% by weight of active 20 agent. 20
The invention is illustrated by the following Examples wherein parts and percentages are by weight and temperatures are in °C.
Formulation Example /: Wettable Powder 25 50 parts of 2-methoxy-N-(2,6-dimethylphenyl)-N-(2-oxo-3-oxazolidinyl)-acetamide are ground with 2 parts of lauryl sulphate, 3 parts sodium lignin sulphonate and 45 parts of finely divided kaolinite until the mean particle size is below 5 microns. The resulting wettable powder so obtained is diluted with water before use to a concentration of between 0.01% to 5% active agent. The resulting spray liquor may be applied by foliar spray a$ well as by root drench application.
30
Formulation Example 2: Granulate
Onto 94.5 parts by weight of quartz sand in a tumbler mixer is sprayed 0.5 parts by weight of a binder (non-ionic tenside) and the whole thoroughly mixed. 5 Parts by weight of powdered 2-methoxy-N-(2,6-dimethylphenyl)-N-(2-oxo-3-oxazolidinyl)-acetamide are then added and thoroughly mixing continued to 35 obtain a granulate formulation with a particle size in the range of from 0.3 to 0.7 mm. The granulate may be applied by incorporation into the soil adjacent the plants to be treated.
Formulation Examples 3 to 6 (wettable powders)
40
45
50
Example
Component a)'1)
copper (II) oxychloride (-56% Cu)
% by weight 3 4
12.65
47
6.25
47
5
12.5
6.25
cuprous oxide (-88% Cu) 29 29
Na laurylsulphate 1111
ligninsulphonate 10 10 10 10
Kaolin 29.5 35.75 39.5 45.75
55
25
30
35
40
45
50
55
111 e.g. 2-methoxy-N-(2,6-dimethylphenyl)-N-(2-oxo-3-oxazolidinyl)-acetamide.
All the components of the formulation are mixed, milled and mixed again in conventional manner.
BNSDOCID: <GB.
i 2058059A l_>
10
GB 2 058 059 A
10
Formulation Examples 7 to 9 (wettable powders)
c
Example
% by weight 7 8
9
9
Component a),1>
25
12.5
6.25
Component b2(2>
50
50
50
10
Na oleoylmethyltauride
2
2
2
15
Condensation product of Na alkyl naphthalene-sulphonate and formaldehyde
5
5
5
silica gel
5
5
5
Kaolin
13
25.5
31.75
20
t1)e.g.2-methoxy-N-(2,6-dimethyiphenyl)-N-(2-oxo-3-oxazolidinyl)-acetamide (z) e.g. Folpet
All the components of the formulation are mixed, milled and mixed again in conventional manner. 25 Formulation Examples 10 to 72 (wettable powders)
% by weight
Example
10
11
12
Component a)'11
25
12.5
6.25
Component b3)121
50
50
50
Na laurylsulphate
1
1
1
lignisulphonate
4
4
4
Silica gel
5
5
5
Kaolin
15
27.5
33.75
(1,e.g. 2-methoxy-N-(2,6-dimethylphenyl)-N-(2-oxo-3-oxazolindinyl}-acetamide (2) e.g. mancozeb
45 The formulation is obtained by mixing the components, subsequently milling the mixture and repeated mixing in conventional manner.
Example 1:2-Methoxy-N-(2,6-dimethylphenyl)-N-{2-oxo-3-oxazolidinyl)-acetamide 11.8 g (0.0375 mol) 2-Ch(oroethy! 2-(methoxy-acetyl)-2-(2,6-dimethy!phenyl)-hydrazinecarboxylate are 50 added portion-wise to a suspension of 2.0 g sodium hydride (in form of about 55% by weight in mineral oil) in 100 ml absolute toluene at room temperature under a blanket of nitrogen. The reaction temperature rises gradually during this addition up to 40°. After the addition is complete the mixture is stirred during 30 minutes without cooling and afterwards cooled to 10°. The unreacted sodium hydride is then destroyed with ethanol, the obtained solution washed with water dried with MgS04 and the solvent removed in vacuo to 55 give the end title compound which is recrystallised from ethanol to yield the title compound as colourless crystals, m.p. 103-104°.
Example la : 2-Chloroethyl-2-(methoxyacetyi)-2-(2,6-dimethylphenyl)-hydrazinecarboxylate The starting material used in Example 1 is obtained as follows:
60 A mixture of 14.7 g (0.06 mol) 2-chloroethyl 2-(2,6-dimethylphenyl)-hydrazinecarboxylate and 16.2 g (0.1 mol) methoxy acetic acid anhydride f(CH30CHzC0)20] are stirred in 100 ml dry toluene during 1 hour at 80°. After cooling, the solution is washed with water, then with a 5% NaHC03 aqueous solution and then again with water.
The solution is dried with MgSO<j and the solvent removed in vacuo to give the title compound of Example 65 1a.
5
10
15
20
25
30
35
40
45
50
55
60
65
BNSDOCID: <GB_
2068059A_I_>
11
GB 2 058 059 A 11
Example lb : 2-Chloroethyl2-(2,6-dimethylphenyl)-hydrazinecarboxylate
To a mixture of 127g (0.935 mol) 2,6-dimethyl. phenylhydrazine, 102.5 g (1.3 mol) pyridine and 400 mi water is added, at 0-5°, 133.5 g (0.935 mol) chloroformic acid (3-chloroethyl ester. After the addition is complete, the mixture is stirred for 2 hours at room temperature, the formed precipitate filtered off, washed 5 with water and dried. The so obtained title compound is recrystallised from toluene to yield colourless 5
crystals, m.p. 74-75°.
According to a preferred alternative procedure of Example 1,1a and 1b, one proceeds as follows:
Example2 : 2-Methoxy-N-(2,6-dimethylphenyl)-N-(2-oxo-3-oxazolidinyl)-acetamide 10 236.1 g (0.75 mol) 2-Chloroethyl 2-(methoxyacetyl)-2-(2,6-dimethylpheny!)-hydrazinecarboxylate, 375 ml 10 xylene and 187 ml water are stirred with external cooling, while 82.5 ml (0.82 mol) of an aqueous solution of sodium hydroxide (containing ~0.4 g NaOH per ml) are added at a rate to maintain the internal temperature at approx. 20°. The mixture is stirred after completion of the addition for 1 hour at 20°, and for 2 hours at 0°. The solid is filtered off, washed with 150 ml water and dried to yield the title compound as a slightly coloured 15 solid, m.p. 102-103°. 15
Example2a : 2-Chloroethyl2-(methoxyacetyl-)-2-(2,6-dimethy/phenyl)-hydrazinecarboxylate
200 g (0.825 mol) 2-Chloroethyl 2-(2,6-dimethylphenyl)-hydrazinecarboxylate in 500 ml xylene are warmed to 80°, and added to warm (80°) solution of 2-methoxy-acetylchloride in 250 ml xylene, prepared in situ by 20 treating 73.5 g (0.826 mol) 2-methoxyacetic acid in 250 ml xylene with 107.1 g (0.9 mol) thionyl chloride at 80° 20 for 2 hours. The mixture is heated for 30 minutes at 80°, then worked up as described in Example 1 a.
Example2b : 2-Chloroethyl2-(2,6-dimethylphertyl)-hydrazinecarboxylate A mixture of 17.7 g (0.1 mol) 2,6-dimethylphenylhydrazine hydrochloride, 21.2 g (0.2 mol) sodium 25 carbonate in 50 ml water and 50 ml xylene are stirred for 30 minutes at room temperature, then cooled to 5°. 25 14.3 g (0.1 mol) chloroformic acid 2-chloroethylester is then added overa period of 1 hour, the temperature being maintained at 5°. The mixture is stirred at 5° for another hour, at the end of which 100 ml water are added, the precipitate thus formed filtered off, washed with water and dried. Further work-up as in Example 1b.
30 In analogous mannerto that described in the preceding Examples 1 and 2 the following compounds of 30 formula I are produced .
BNSDOCID: <GB 2058059A_I_>
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13
GB 2 058 059 A 13
Ex. No.
r3
p,4
*5
r6
R7
r8
r9
r10
0*0
• 0
22
h h
h h
ci ci h
l!]
173-4
23
h h
h h
ch3
ch3
h ch2ND
139-41
24
h h
h h
ch3
ch3
4-ch3
ch2och3
oil
25
h
H
h h
ch3
c2h5
H
ch2ci oil
26
h h
h h
CH3
CH3
3-cl ch2och3
90-2
27
H
h
H
H
ch3
ck3
3-Br ch2och3
96-7
28
h h
H
h
CH3
ch3
3-Br ch2ci
182-3
29
h h
h h
ch3
CH3
3-Br
145-8
30
h h
h h
ch3
Br
4-ch3
ch2och3
125-6
31
h h
h h
ch3
Br
4-ch3
ch2ci
124-6
32
h h
h h
cfi3
Br
4-ch3
t1j)
193-4
33
h h
h h
ch'3
ch3
h choch-
90-4
ch3
34
h h
h h
ck3
ch L..I3
h
149-52
35
h h
h h
ch3
ch3
4-Cl ch2c1
gum
36
h h
tt h
ch3
ch3
4-cl
I!i!
164-5
37
h h
h h
c2h5
c2h5
h ch2°ch3
109-12
38
h h
h h
ch3
ch3
h
CH2OC3H?(n)
oil
BNSDOCID: <GB 2058059A_I_>
14 GB 2 058 059 A
14
ex. !!o.
r3
*4
r5
*6
r7
rs r9
r10
m.p.
(°c)
39
h h
h h
ch3
ch3
h ch2oc4h9(n)
40
h h
h h
ch3
ch3
h ch-och-c.h,
* 1 i j
ch3
41
h h
h h
ch3
ch3
h chpch2ch=ch2
9 8-100
42
h h
h h
ch3
ch3
h ch2och2c=ch
91-93
43
h h
h h
ch3
ch3
h
107-8
44
h
H
CH3
H
ch3
ch3
h ch2och3
79-80
45
h h
h ii
CK3
ch3
h ch2'd
56
46
h h
h h
c2h5
c2h5
h tfll
142-4
47
H
H
a
H
"2h5
c2h5
h ch2c1
88-9
48
H
H
H
H
3r
Br
H
ch2och3
150-2
49
H
H
H
H
31
CI
4-Cl ch2och3
128-9
50
H
H
h h
"2h5
c2h5
4-Cl ch2och3
114-6
51
H
H
h-
h
Br
CI
4-CH3
ch2och3
131-4
32
h h
h
H
"h3
c2h5
h ch2och3
96-8
53
h h
h h
ch3
ch3
4-Br ch2och3
137-8
BNSDOCID: <GB 2058059A_I_»
15
GB 2 058 059 A
15

Claims (74)

  1. CLAIMS 1. A compound of formula I
    wherein R7 and R8, independently, are C-1.4 aikyl, halogen or Ci^aikoxy, and R9 is hydrogen, Chalky! or halogen,
    R2 is CO-Rioi
    20 wherein R10 is C^alkoxy-C^alkyl, Ci^alkyl-thio-C^alkyl, 2-furyl, 2-tetrahydrofuryl, halogenated 2-furyl, halogenated 2-tetrahydrofuryl, 1 -i mi dazolym ethyl, 1-pyrrazolymethy-, 2-tetrahydrofuryloxy methyl, 2-tetrahydropyranyloxymethyl, or C^halogenalkyl, and R3, R4, R5 and R6 are independently hydrogen or C-i^alkyl.
  2. 2. A compound of Claim 1 wherein R3, R4, Rs and R6 are hydrogen.
  3. 25 3. A compound according to Claim 2 wherein R2 is -COCH2OCH3, -COCH2OC2H5, -CO-(2-furyl) or -CO-(5-halo-2-furyl), R7 and Rs are independently CH3, CI or Br and Rg is H, Ci, Br or CH3.
  4. 4. A compound according to Claim 3 wherein R7 and Rs are identical.
  5. 5. A compound of Claim 4, wherein R7< R8, Rg and R10 are CH3, CH3, H and CH2OCH3 respectively.
  6. 6. A compound of Claim 4 wherein R7, R3, Rs and R10 are CH3, CH3, H and CH2OC2H5 respectively. 30 7. A compound of Claim 3 wherein R
  7. 7,R8, Rg and R10 are CH3, CI, H and CH2OCH3 respectively.
  8. 8. A compound of Claim 4, wherein R7, Rs, Rg and R10 are CH3, CH3, H and 2-furyl respectively. >
  9. 9. A compound of Claim 4 wherein R7, R8, Rg and R10are CH3, CH3( 4-Cl and CH2OCH3 respectively.
  10. 10. A compound of Claim 2 wherein R7, R8, R9 and R10 are CH3, CH3, H and CH2SCH3 respectively.
  11. 11. A compound of Claim 2 wherein R7, Rs, R9 and R,0 areCH3, CH3, H and CH2CI respectively. 35
  12. 12. A compound of Claim 2 wherein R7, Rs, R9 and R10 areCH3, CI, H and CH2CI respectively.
  13. 13. A compound of Claim 2 wherein R7, R8, Rg and R10 are CH3, CH3, H and CH2OCH(CH3)2 respectively.
  14. 14. A compound of Claim 2 wherein R7, Rs, R9 and R10 are CH3, CI, H and CH2OCH(CH3)2 respectively.
  15. 15. A compound of Claim 3 wherein R7, Ra, R9and R10areCH3, CI, H and 2-furyl respectively.
  16. 16. A compound of Claim 2 wherein R7, Rs, Rgand R1fl areCH3, CH3, H and CH2SC4H9(n) respectively. 40
  17. 17. A compound of Claim 2 wherein R7, Ra, Rgand R10are CH3, CI, H and CH2SC4Hg(n) respectively.
  18. 18. A compound of Claim 2 wherein R7( Ra, Rgand R10are CH3, CH3, H and CHBrC2H5 respectively.
  19. 19. A compound of Claim 2 wherein R7, Ra, Rg and R10 are CH3, CH3, H and CHClCH3 respectively.
  20. 20. A compound of Claim 2 wherein R7, R8, R9 and R10 are CH3, CH3, H and CH2Br respectively.
  21. 21. A compound of Claim 4 wherein R7/ R8, R9and R10 are CH3, CH3, H and 5-Br-2-furyl respectively. 45
  22. 22. A compound of Claim 4 wherein R7, R8, R9 and R10 are CI, CI, H and CH2OCH3 respectively.
  23. 23. A compound of Claim 2 wherein R7, Rs, R9 and R10 are CI, CI, H and CH2CI respectively.
  24. 24. A compound of Claim 4 wherein R7, R8, Rg and R10 are CI, CI, H and 2-furyl respectively.
  25. 25. A compound of Claim 2 wherein R7, R8, Rgand R10are CH3, CH3r H and 1-pyrazolylmethyl respectively.
  26. 26. A compound of Claim 4 wherein R7, R8, R9 and Ri0 are CH3, CH3,4-CH3 and CH2OCH3 respectively. 50
  27. 27. A compound of Claim 2 wherein R7, R8, Rg and Ri0 are CH3, C2HS, H and CH2CI respectively.
  28. 28. A compound of Claim 4 wherein R7, R8, Rg and R10 are CH3, CH3r 3-Cl and CH2OCH3 respectively.
  29. 29. A compound of Claim 4 wherein R7, R8, Rg and R10 are CH3, CH3,3-Br and CH2OCH3 respectively.
  30. 30. A compound of Claim 2 wherein R7, Rs, Rg and R10 areCH3, CH3,3-Br and CH2CI respectively.
  31. 31. A compound of Claim 4 wherein R7, R8, R3 and RI0 are CH3, CH3,3-Br and 2-furyl respectively. 55
  32. 32. A compound of Claim 3 wherein R7, Rs, R9 and R10 are CH3, Br, 4-CH3 and CH2OCH3 respectively.
  33. 33. A compound of Claim 2 wherein R7, R8, Rg and R10 are CH3, Br, 4-CH3 and CH2CI respectively.
  34. 34. A compound of Claim 3 wherein R7, Rs, R9 and R10 are CH3, Br, 4-CH3 and 2-furyl respectively.
  35. 35. A compound of Claim 2 wherein R7< Rs, R9 and R10 are CH3, CH3, H and CH(CH3)OCH3 respectively.
  36. 36. A compound of Claim 2 wherein R7, Ra, Rg and R10 are CH3, CH3, H and 2-tetrahydrofuryl respectively. 60
  37. 37. A compound of Claim 2 wherein R7, R8, Rg and R10 are CH3, CH3,4-Cl and CH2CI respectively.
  38. 38. A compound of Claim 2 wherein R7, R8, Rg and R10 are CH3, CH3,4-Cl and 2-furyl respectively.
    38. A compound of Claim 2 wherein R7, R8, Rg and R10 are C2H5, C2H5, H and CH2OCH3 respectively.
  39. 39. A compound of Claim 2 wherein R7, R8, Rg and R10 are C2H5, C2Hs, H and CH2OCH3 respectively.
  40. 40. A compound of Claim 2 wherein R7, R8, Rg and R10 are CH3, CH3, H and CH2OC3H7(n) respectively. 65
  41. 41. A compound of Claim 2 wherein R7, R8, R9 and R10 are CH3, CH3, H and CH2OC4Hg(n) respectively.
    BNSDOCID: <GB 2058059A_J_>
    5
    10
    15
    20
    25
    30
    35
    40
    45
    50
    55
    60
    65
    16
    GB 2 058 059 A
    16
  42. 42. A compound of Claim 2 wherein R7, Ra, R9 and R10 are CH3, CH3, H and CH2OCH(CH3)C2H5 respectively.
  43. 43. A compound of Claim 2 wherein R7, Ra, R9 and R10 are CH3( CH3, Hand CH2OCH2-CH2 respectively.
  44. 44. A compound of Claim 2 wherein R7, R3t R9 and R10 are CH3, CH3, H and CH2OCH2-C=CH respectively.
  45. 5 45. A compound of Claim 2 wherein R7, Rs, R9and R10 are CH3,CH3r Hand 2-tetrahydropyrany(oxymethyl 5 respectively.
  46. 46. A compound of Claim 2 wherein R7, RB, R9and Rio are CH3,CH3, H and 1-pyrazolylmethyl respectively.
  47. 47. A compound of Claim 2 wherein R7, Ra, R9 and R10 are C2HS/ C2H5, H and 2-furyl respectively.
  48. 48. A compound of Claim 2 wherein R7/ Re. R9and Ri0areC2H6,. C2H5, H and CH2CI respectively. -
  49. 10 49. A compound of Claim 4 wherein R7, R8r R9 and R10 are Br, Br, H and CH2OCH3 respectively. 10
  50. 50. A compound of Claim 4 wherein R7, Rs, R9 and Rno are CI, CI, 4-Cl and CH2OCH3 respectively.
  51. 51. A compound of Claim 2 wherein R7, RB, R9 and Ri0areC2H5, C2HS,4-CI and CH20CH3 respectively.
  52. 52. A compound of Claim 3 wherein R7, Ra, Rg and Rio are Br, CI, 4-CH3 and CH2OCH3 respectively.
  53. 53. A compound of Claim 2 wherein R7, Ra, R9and R10areCH3,C2Hs, H and CH2OCH3 respectively.
  54. 15 54. A compound of Claim 2 wherein R7,R8, R9and Rn0 are CH3, CH3,4Br and CH2OCH3 respectively. 75
  55. 55. A method of combating phytopathogenic fungi in plants, seeds or soil, which comprises applying to the plants, seeds or soil a fungicidally effective amount of a compound claimed in any one of claims 1 to 54.
  56. 56. A method of combating phytopathogenic fungi in plants or soil according to Claim 55, which comprises applying to said locus 0.05 to 5 kg of a compound claimed in any one of Claims 1 to 54 per hectare
    20 treated locus. 20
  57. 57. A method according to Claim 56, in which the dosage rate is from 0.1 to 3 kg of a compound claimed in any one of Claims 1 to 54 per hectare treated locus.
  58. 58. A method of combating phytopathogenic fungi in seeds according to Claim 55, which comprises applying from 0.05 to 0.5 g of a compound claimed in any one of claims 1 to 54 per kg seed.
  59. 25 59. A method of combating phytopathogenic fungi in a locus which comprises applying to the locus to be 25 treated fungicidally effective amounts of a component a) comprising a compound of formula I as defined in any one of Claims 1 to 54, and of a component b) selected from a component bl) a copper fungicide or a component b2) captan orfolpet or a component b3) mancozeb or maneb.
  60. 60. A method according to Claim 59, wherein component b) is mancozeb.
  61. 30 61. A method according to Claim 59, wherein component b) is cuprous oxide, copper (II) oxychloride, 30 cupric hydroxide or a mixture of copper (II) calcium sulphate with copper (II) oxychloride.
  62. 62. A method according to any one of Claims 59 to 61 which comprises applying component a) ata rate of 100-400 g per hectare and component b) at a rate of 200-2000 g/ha.
  63. 63. A method according to Claim 62 which comprises applying the components a) and b) in a weight
    35 ratio of 1:1 to 1:10 of componenta): component b). 35
  64. 64. A method according to Claim 63 wherein the weight ratio component a) : component b) is 1:2 to 1:7.
  65. 65. A composition comprising a compound of formula I as defined in any one of Claims 1 to 54 in association with an agriculturally acceptable carrier or diluent.
  66. 66. Afungicidal composition comprising a component a) and a component b) as defined in Claim 59 in a
    40 weight ratio of 1:1 to 1:10 of componenta): componentb). 40
  67. 67. A fungicidal composition wherein the weight ratio component a): component b) is from 1:2 to 1:7.
  68. 68. A composition according to any one of Claims 65 to 67 in comprising from 0.01 to 90% by weight of a compound of formula I as claimed in any one of Claims 1 to 54 or mixtures thereof with component b) as defined in Claim 59.
  69. 45 69. Concentrate forms of compositions according to any one of Claims 65 to 68 comprising from 2 to 80% 45 of component a) or of a mixture of component a) and component b) as defined in Claim 59.
  70. 70. Liquid application forms of compositions according to any one of Claims 65 to 68 comprising from 0.01 to 20% by weight of component a) or of a mixture of component a) and component b) as defined in Claim 59.
    50
  71. 71. A process forthe production of a compound of formula I as claimed in Claim 1 characterized by 50
    intramolecular condensation of a compound of formula II
    u 0 rt. x*
    h 11 3\ / 6 / 4 yi} - c - o - c c - if II
    55 Ri 55
    \
    1
    o c - r 11 1g wherein Ri, Ra, R4, R=, Rs and Ri-j are as defined in Claim 1 and Y is halogen.
    60
  72. 72. A process for the production of a compound of formula I substantially as hereinbefore described with 60 reference to any one of the Examples.
  73. 73. A compound of formula I whenever produced by a process according to Claim 71 or 72.
  74. 74. A compound of formula II
    : <GB_
    S 2058059A l_>
    17
    GB 2 058 059 A
    17
    O Rp Ri H » \ / 6 4 ytA - C - O - C C - Y II
    r1 - k\
    5 S " RI0
    0
    wherein R1x R3, R„, R5, R6 and R10 are as defined in Claim 1 and Y is halogen.
    Printed for Her Majesty's Stationery Office, by Croydon Printing Company Limited, Croydon, Surrey, 1381. Published by The Patent Office, 25 Southampton Buildings, London, WC2A 1AY, from which copies may be obtained.
    BNSDOCID: <GB 2058059A_J_>
CY1247A 1979-08-16 1980-08-13 N-acylamino-2-oxo-3-oxazolidine derivatives and their use as fungicides CY1247A (en)

Applications Claiming Priority (2)

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GB7928603 1979-08-16
GB8026318A GB2058059B (en) 1979-08-16 1980-08-13 N-acylamino-2-oxo-3-oxazolidine derivatives and their use as fungicides

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CY1247A true CY1247A (en) 1984-08-31

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DE3231606A1 (en) * 1981-02-09 1983-02-10 Sandoz Ag FUNGICIDES
IT1168031B (en) * 1981-10-01 1987-05-20 Montedison Spa FUNGICIDAL COMPOUNDS
DE4304172A1 (en) 1993-02-12 1994-08-25 Bayer Ag Fungicidal active ingredient combinations
BRPI0509124A (en) 2004-04-30 2007-08-28 Basf Ag fungicidal mixtures, agents, process to combat harmful fungi, seed, and use of a compound
EP1835807A1 (en) 2004-12-17 2007-09-26 Devgen N.V. Nematicidal compositions
ITMI20051558A1 (en) 2005-08-09 2007-02-10 Isagro Spa MIXTURES E-O SYNERGIC COMPOSITIONS CIN HIGH ACTIVITY FEATURES
EP2489266A3 (en) 2006-09-18 2012-10-24 Basf Se Pesticidal mixtures comprising an anthranilamide insecticide and a fungicide
WO2008071714A1 (en) 2006-12-15 2008-06-19 Rohm And Haas Company Mixtures comprising 1-methylcyclopropene
EP2679095A1 (en) 2007-02-06 2014-01-01 Basf Se Pesticidal mixtures
EP2392662A3 (en) 2007-04-23 2012-03-14 Basf Se Plant productivity enhancement by combining chemical agents with transgenic modifications
EP2205082B1 (en) 2007-09-26 2012-04-04 Basf Se Ternary fungicidal compositions comprising boscalid and chlorothalonil
WO2011026796A1 (en) 2009-09-01 2011-03-10 Basf Se Synergistic fungicidal mixtures comprising lactylates and method for combating phytopathogenic fungi
EP2417853A1 (en) 2010-08-05 2012-02-15 Basf Se Synergistic fungicidal and insecticidal mixtures comprising a fungicide and an insecticide
AU2011347752A1 (en) 2010-12-20 2013-07-11 Basf Se Pesticidal active mixtures comprising pyrazole compounds
EP2481284A3 (en) 2011-01-27 2012-10-17 Basf Se Pesticidal mixtures
ES2660555T3 (en) 2011-03-23 2018-03-22 Basf Se Compositions containing ionic, polymeric compounds comprising imidazolium groups
US20140200136A1 (en) 2011-09-02 2014-07-17 Basf Se Agricultural mixtures comprising arylquinazolinone compounds
BR122019015109B1 (en) 2012-06-20 2020-04-07 Basf Se pesticide mixture, composition, agricultural composition, methods for combating or controlling invertebrate pests, for the protection of growing plants or plant propagation material, for the protection of plant propagation material and the use of a pesticide mixture
WO2014056780A1 (en) 2012-10-12 2014-04-17 Basf Se A method for combating phytopathogenic harmful microbes on cultivated plants or plant propagation material
US10759767B2 (en) 2012-12-20 2020-09-01 BASF Agro B.V. Compositions comprising a triazole compound
EP2783569A1 (en) 2013-03-28 2014-10-01 Basf Se Compositions comprising a triazole compound
EP2835052A1 (en) 2013-08-07 2015-02-11 Basf Se Fungicidal mixtures comprising pyrimidine fungicides
WO2015036059A1 (en) 2013-09-16 2015-03-19 Basf Se Fungicidal pyrimidine compounds
EP3046915A1 (en) 2013-09-16 2016-07-27 Basf Se Fungicidal pyrimidine compounds
EP2979549A1 (en) 2014-07-31 2016-02-03 Basf Se Method for improving the health of a plant
JP2017538860A (en) 2014-10-24 2017-12-28 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ Non-amphoteric quaternizable water-soluble polymer for modifying the surface charge of solid particles

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