Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
  • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
  • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
  • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
  • C07D307/12—Radicals substituted by oxygen atoms

Definitions

• the present invention relates to new ca-rbamic acid esters which have fungitoxic properties, and to a process for the production thereof.
• One object of the present invention consists in disclosing new carbamic acid esters which have fungitoxic properties. Another object consists in providing several processes for the production of these new carbamic acid esters. It is also an object of the invention to provide new agents for combating phytopathogenic fungi. Further objects can be seen from the following description and the examples.
• R stands for hydrogen, alkyl, alkenyl, alkox'y, dialkylamino, dialkenylamino, alkylmercapto, alkenylmercapto, halogen and/or nitro,
• A stands for alkylene with 1 to carbon atoms
• R stands for chlorine, alkoxy, alkylmercapto, cycloalkoxy or a 'heterocyclic radical
• n stands for a number from 1 to 5
• R preferably stands for hydrogen, alkyl, alkenyl, alkoxy, dialkylamino and alkylmercapto, each with 1 to 4 carbon atoms in the alkyl radicals, for dialkenylamino and alkenylmercapto, each with 2 to 4 carbon atoms in the alkenyl radicals, as well as for chlorine, bromine and nitro.
• R preferably stands for chlorine, alkoxy with 1 to 10 carbon atoms, alkylmercapto with 1 to 4 carbon atoms, cycloalkoxy with 5 to 6' ring atoms and heterocyclic radicals with 5 to 6 ring atoms which preferably contain oxygen, nitrogen or sulphur.
• phenols which can be used according to the invention, there may be mentioned: phenol, 4-. methyl-, 3-methyl-4-chloro-, 2-allyl-, 3-methoxy-, 2- ChlOI'Or, 3-chloro-, 4-chloro-, 2,4-dichloro 2,4-dichloro-, 6-nitro-, 2,4,6-tri'chloro-, pentachloro, 2-chlo1ro4-nitro-, 3-methyl-4-dimethylamino-, 2-diallylamino-, 4-methylmercapto 3amethyl-4-methylmercapto-, 3,5-dimethyl-4- methylmercapto-, 2-isopropyl-4-methylmercapto-, 3-lmethyl-4-allylmercapto-phenol.
• isocyanates or amines to be used according to the invention are l-chloroethyl-2-, l-chlorobutoxypropyl-, 1-chloro-n-'hexyl-6-, methoxymethyl-, methoxypropyl-, ethoxypropyl-, sec. buto-xypropyl-, cyclohexoxypropyl-, -isopropyloxypropyl-, 2-ethylhexoXypropyl-, methylmercaptoethyl-, ethylmercaptopropyl-isocyanate or -amine.
• the process (a) is expediently carried out in the presence of inert organic solvents within a temperature range between -50 and +150 C., and bases, preferably tertiary amines such as triethylamine and pyridine, are optionally added as catalysts.
• the first step of process (b) is expediently carried out at pH values below 6 in aqueous or alcoholic solvents Within a temperature range between about 50 and +150 C.
• the second step of this process is expediently performed in the presence of inert organic solvents within a temperature range of about 20 to C.
• the first step of process (c) is expediently carried out at pH values between 6 and 9 in the presence of inert organic solvents, with the addition of an inorganic agent splitting off acid, such as a sodium hydroxide solution, at temperatures between and 100 C.
• the second step of this process is expediently performed in the presence of inert organic solvents at temperatures between 50 and 150 C.
• Suitable inert organic solvents are, for example, hydrocarbons, such as benzine and benzene; chlorinated hydrocarbons, such as methylene chloride and dichlorobenzene; ethers, such as diethyl ether and dioxan; ketones, such as acetone and cyclohexanone, as well as acetonitrile and dimethyl formamide.
• hydrocarbons such as benzine and benzene
• chlorinated hydrocarbons such as methylene chloride and dichlorobenzene
• ethers such as diethyl ether and dioxan
• ketones such as acetone and cyclohexanone, as well as acetonitrile and dimethyl formamide.
• reaction components are used in about equimolar amounts, but the phosgene can also be employed in excess.
• the reaction is carried out in the, usual manner. Working up is performed by known methods;
• the compounds according to the invention have a strong fungitoxic effect and are distinguished by a broad spectrum of activity. Due to their low toxicity towards warm-blooded animals, they are suitable for combating undesirable fungus growth. Their good compatibility with higher plants enables them to be used as plant protective agents against fungus diseases.
• the compounds according to the invention have proved especially satisfactory for controlling rice diseases. They have an excellent protective effect when combating Piricularia oryzae in rice.
• the substances according to the invention also have an especially good activity against a number of other fungi, such as species of Mycosphaerella, Cercospora, Corticium, Alternaria, Septoria, and against Botrytis cinerea.
• the compounds according to the invention also have a fungitoxic acivity against fungi which attack the plant from the soil and sometimes cause tracheomycoses, such as Phz'alophora cinerescens, Verticillium alboatrum, Fusarizzm oxysp.f.cubense, Fusarium oxysp.f.dianthi.
• fungitoxic acivity against fungi which attack the plant from the soil and sometimes cause tracheomycoses, such as Phz'alophora cinerescens, Verticillium alboatrum, Fusarizzm oxysp.f.cubense, Fusarium oxysp.f.dianthi.
• the compounds according to the invention as leaf fungicides, have mainly a protective effect, a mixture with curative agents is advantageous.
• Organic mercury compounds such as phenyl-mercury acetate, and also antibiotics, such as Plasticidin S, are suitable for this purpose.
• a substantial reduction of the mercury content can be achieved in the mixed preparation.
• the disadvantages occurring when organic mercury compounds are used by themselves, such as the toxicity towards warm-blooded animals, can thus be reduced.
• preparations of protective and of curative effect as in the mixture mentioned above, an increased effectiveness can be attained.
• the compounds according to the invention can be transformed into the usual formulations, such as emulsifiable concentrates, spray powders, pastes, soluble powders, dusts and granulates. These are prepared in known manner, for example by extending the active ingredients with solvents and/ or carriers, if desired with the use of emulsifiers and/or dispersing agents (cf. Agricultural Chemicals, March 1960, pages 35-38).
• Suitable auxiliaries for this purpose are mainly solvents, such as aromatics (e.g. xylene, benzene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. petroleum fractions), alcohols (e.g.
• emulsifiers such as non-ionic and anionic emulsifiers (e.g. polyoxyethylenefatty acid esters, polyoxyethylene-fatty alcohol ethers, alkylsulphonates and arylsulphonates), and dispersing agents, such as lignin, sul.
• the compounds according to the invention can be pres ent in the formulations in admixture with other known active ingredients.
• the formulations generally contain between 0.1 and 95, preferably between 0.5 and 90, percent by weight of active compound.
• the compounds to be used or their preparations are applied in usual manner, for example by spraying, dusting, sprinkling or atomizing.
• the active ingredient can be used in concentrations between 0.2 and 0.005%, dependent upon the intended application. In special cases, however, it is possible to exceed or to remain below this range of concentration.
• Solvent 1 part by weight of acetone Dispersing agent: 0.05 part by weight sodium oleate
• Other additives 0.2 part by weight gelatin
• Water 98.75 parts by weight H O
• the amount of active compound required for the desired concentration of the active compound in the spray liquid is mixed with the stated amount of solvent, and the concentrate obtained is diluted with the stated amount of water containing the stated additives.
• Example B Piricularia test/solid preparation of active compound Solvent: 10 parts by weight acetone Dust Base: 100 parts by weight 0.5% Mg. stearate 4.0% silicic acid 0.5% Mg. stearate Piricularz'a, oryzae and placed in a room at 2426 C.
• n n 0003 A S M mm m u W g E Q Q n n n H e n O 0 353: 0 6 C m I 0 O h 33% 000 00 n F 0002 00 U 0001 v n 1 1 m a C P 4 C 0 C r. :1 2 3 0024 24. n u 004 n 04 u 0004 T m .h h e.mfl 0 d 1 52? u n n m h w m m n m W 3.858 0013 14 n n 004 04.
• hosgene is re- (1) C1 moved in a vacuum. After the mixture is filtered off with 01 OG""NH(CH2)GCl 2,4 dichlorophenyl N-(6-chloro-n -hexyl) carbamatet 73 MP. 55-56 c.
• D is alkylene of l-8 carbon atoms and R is a member selected from the group consisting of alkoxy of 1-10 carbon atoms, chloro, cycloalkoxy of 56 carbon atoms in the ring, alkyl mercapto of 1-4 carbon atoms and 12 2.
• the compound of the formula D is allzylene of 18 carbon atoms; and R is alkoxy of 1-l0 carbon atoms. 3.
• the compound of the formula 4 The carbamic acid ester of the formula 5.
• the carbamic acid ester of the formula References Cited UNITED STATES PATENTS 7/1960 Jones et al. 167-30 X 4/1964 Surrey et al. 260-479 9/1965 Heiss et al. 260-479 FOREIGN PATENTS 5/1963 Belgium. 11/1962 Germany.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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Publications (1)

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Family Applications (1)

Country Status (8)

Cited By (2)

Citations (5)

• 1964
  • 1964-12-28 CH CH1670264A patent/CH441861A/de unknown
  • 1964-12-29 IL IL22692A patent/IL22692A/xx unknown
• 1965
  • 1965-01-05 US US423596A patent/US3376335A/en not_active Expired - Lifetime
  • 1965-01-25 NL NL6500915A patent/NL6500915A/xx unknown
  • 1965-01-25 BE BE658752D patent/BE658752A/xx unknown
  • 1965-01-25 ES ES0308529A patent/ES308529A1/es not_active Expired
  • 1965-01-25 GB GB3262/65A patent/GB1025049A/en not_active Expired
  • 1965-01-25 FR FR3219A patent/FR1452615A/fr not_active Expired
  • 1965-03-23 ES ES0310863A patent/ES310863A1/es not_active Expired

Patent Citations (5)

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