Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
  • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
  • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
  • C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Definitions

• DE-OS 2 130 673 discloses benzhydryl imidazole derivatives with alkyl substitution in the imidazole ring.
• 1-benzyl- and 1-tetrahydronaphthyl-imidazole- (5) -carboxylic acids and their esters have already been described (J. Med. Chem. 15, 336-337 (1972)).
• Benzhydryl-imidazole derivatives with a carboxyl function in the imidazole radical are not yet known.
• compounds of the formula I which contain hydrogen or a carbalkoxy group in the 4-position of the imidazole ring and an —SH group in the 2-position.
• the latter can be dehydrated in a known manner, for example by means of iodine, oxygen, hydrogen peroxide or sulfuryl chloride, disulfides of the formula III being obtained.
• the SH group can also be eliminated from the compounds obtained in the first stage by desulfurization, for example by 15 percent nitric acid at 30 to 35 ° C. or nickel at 50-100 ° C.
• the desulfurized compounds can then be halogenated or hydroxymethylated in the 2-position in the usual way.
• the hydroxymethyl group can be introduced, for example, by using methanolic or aqueous formaldehyde solution at elevated temperature, preferably 130 to 140 ° C. in the pressure vessel.
• the group -CO-Rg serves as a protective group, which prevents a double reaction on both nitrogen atoms of the imidazole ring.
• the starting materials of the formula V can be obtained by acylation of compounds of the formula VIII on nitrogen atom 1.
• the reaction of the compounds of the formula V with those of the formula VI results in a quaternization on the nitrogen atom 3.
• X generally represents a group which enables the quaternization of the imidazole ring; as such halogen (CI, Br) or an alkyl or arylsulfonyl group (mesyl, tosyl) is preferred.
• esters can be saponified to free acids or their salts in a known manner.
• Free acids such as those formed according to a) to f) by saponification of ester groups or according to g) by saponification of cyano groups, can furthermore, optionally via the acid chlorides, into other esters, thiolesters, amides, anilides or hydrazides of the formula - CO-R to be transferred. If two ester groups are present, one of them can be saponified and decarboxylated.
• the nitrate was suspended in 100 ml of chloroform. After adding about 60 ml of a 1N sodium hydroxide solution, the entire nitrate went into solution. 17.8 g (61% of theory) of 1-benzhydryl-5-methoxycarbonyl-imidazole could be isolated from the chloroform solution.
• the compounds according to the invention can be used in many ways as plant treatment agents in agriculture and horticulture. They are effective growth regulators, herbicides and fungicides. They can also be used to control moss, phytopathogenic bacteria and as antifungals
• the invention therefore also relates to agents for use in agriculture and horticulture and as antifungals, plant growth-regulating and herbicidal agents and agents for combating fungi and phytopathogenic bacteria.
• the active compounds according to the invention are converted, in a manner known per se, alone or in combination with other active compounds or nutrients into the customary formulations, such as powders, dusts, pastes, granules, solutions, foams, emulsions and suspensions.
• Solvents, liquefied gases, emulsifiers, dispersants, foam generators and solid carrier materials such as those available for processing non-crop protection agents or pharmaceuticals are suitable for mixing and stretching the active ingredients.
• the compounds can be used within a substantial concentration range of about 0.00005 to 2%.
• the active ingredients can also be used in higher concentrations, even in pure form, e.g. microfine ground, find use.
• the active ingredient concentration per ha of soil is generally 0.01 kg of active ingredient.
• 20 to 50 percent wettable powders which contain the usual proportions of inert, cell pitch and wetting agents, and possibly also adhesives, 15 to 30 percent emulsion concentrates and 5 percent granules in addition to dusts of different active ingredient concentrations are preferred.
• Preparations for the treatment of skin fungi usually contain 0.5 to 2% of the active ingredient.
• the compounds according to the invention show excellent growth-inhibiting activity, e.g. for cereals, broad beans and ornamental turf as well as in the germ test for linseed and oat grains.
• the harvest can be facilitated and the yield increased while the quality of the harvested products can be increased.
• the nutrient supply to the ears is improved and storage losses can be avoided.
• the protein content in cereals and soybeans as well as the sugar content in sugar beet and cane can be increased by using growth regulators.
• Other areas of application are, for example, the optimization of cuttings and leaf growth in tobacco plants.
• the growth of lawn, herbs and woody plants can be controlled, which reduces the maintenance costs.
• the use of mechanical harvesting aids is made possible or at least made cheaper by the use of growth regulators.
• good adaptation to the qualitative and time requirements of the market can be achieved.
• the compounds according to the invention also have very good herbicidal properties, particularly in the pre-emergence, against a large number of economically important harmful grasses and dicotyledon weeds. On the other hand, they are compatible with some crops of agricultural and horticultural importance, such as cotton, corn, rapeseed, beans, etc., so that they are suitable for selective weed control.
• the compounds also have an excellent, partially systemic action against phytopathogenic fungi and are therefore outstandingly suitable as crop protection agents. They show a good fungicidal activity e.g. against rust fungi, Phytophthora infestans, Plasmopara viticola, Venturia inaequalis, Phoma betae and Botrytis cinerea as well as against skin fungi such as Trichophone mentagrophytes and Microsporium canis.
• the compounds have an excellent fungicidal action against Piricularia oryzae and powdery mildew on cucumber, cereals (wheat and barley), apples and ornamental plants. Of particular note is the excellent fungicidal activity of the compounds against benzimidazole-resistant mildew species.
• the fungicidal agents can be used in a conventional manner e.g. be formulated as dusts, wettable powders, dispersions and emulsion concentrates. Their total active substance content is preferably 10 to 90% by weight. They also contain the usual adhesives, wetting agents, dispersing agents, fillers and carriers.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Plural Heterocyclic Compounds (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Applications Claiming Priority (2)

Publications (2)

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Family Applications (1)

Country Status (18)

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• 1977
  • 1977-07-19 DE DE19772732531 patent/DE2732531A1/de not_active Withdrawn
• 1978
  • 1978-07-06 EP EP78100314A patent/EP0000373B1/de not_active Expired
  • 1978-07-06 DE DE7878100314T patent/DE2860407D1/de not_active Expired
  • 1978-07-12 ES ES471660A patent/ES471660A1/es not_active Expired
  • 1978-07-17 PH PH21387A patent/PH14312A/en unknown
  • 1978-07-17 GR GR56806A patent/GR74141B/el unknown
  • 1978-07-17 IT IT25809/78A patent/IT1097833B/it active
  • 1978-07-17 DD DD78206766A patent/DD138877A5/xx unknown
  • 1978-07-17 IL IL55149A patent/IL55149A/xx unknown
  • 1978-07-17 EG EG445/78A patent/EG13351A/xx active
  • 1978-07-17 US US05/925,546 patent/US4182624A/en not_active Expired - Lifetime
  • 1978-07-18 AU AU38116/78A patent/AU516238B2/en not_active Expired
  • 1978-07-18 PT PT68316A patent/PT68316A/pt unknown
  • 1978-07-18 ZA ZA00784094A patent/ZA784094B/xx unknown
  • 1978-07-18 DK DK320678A patent/DK320678A/da unknown
  • 1978-07-18 BR BR7804613A patent/BR7804613A/pt unknown
  • 1978-07-18 AT AT0518878A patent/AT367601B/de not_active IP Right Cessation
  • 1978-07-18 CA CA307,637A patent/CA1095910A/en not_active Expired
  • 1978-07-18 JP JP8684478A patent/JPS5422367A/ja active Pending
• 1979
  • 1979-03-31 ES ES479162A patent/ES479162A1/es not_active Expired
  • 1979-03-31 ES ES479160A patent/ES479160A1/es not_active Expired
  • 1979-03-31 ES ES479161A patent/ES479161A1/es not_active Expired
  • 1979-03-31 ES ES479159A patent/ES479159A1/es not_active Expired
  • 1979-03-31 ES ES479163A patent/ES479163A1/es not_active Expired
  • 1979-03-31 ES ES479158A patent/ES479158A1/es not_active Expired

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