Fungicides for the control of take-all disease of plants

Inactive Publication Date: 2000-02-08
MONSANTO TECH LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention provides a method of controlling disease caused by Gaeumannomyces species in plants comprising applying to the plant locus, that is, the plant itself, its seed, or the soil, a fungicidally effect

Problems solved by technology

Take-All disease is a serious problem in the production of cereals, particularly wheat and barley.
The fungus infects the roots of the plant, and grows throughout the root tissue, causing a black rot.
The growth of the fungus in the roots and lower stem prevents the plant from obtaining sufficient water and/or nutrient

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example a

2-Chloro-6-(trimethylsilyl)benzoic acid

2-Chlorobenzoic acid (3.91 g, 25 mmol), THF (60 mL), and TMEDA (8.6 mL, 57 mmol) were stirred under nitrogen and cooled to -100.degree. C. 1.3M s-BuLi in cyclohexane (0.055 mol, 42.3 mL) was added dropwise keeping the temperature below -80.degree. C. After the addition was complete TMSCl (2.7 g, 25 mmol) was added dropwise and the resulting mixture was allowed to stir and slowly warm to -30 C. 25% citric acid (100 mL) was added and the mixture was extracted with two 50 mL portions of ether, which were then combined and washed three times with water, dried (MgSO.sub.4) and concentrated. The crude product was purified by HPLC, eluting with 2:3 ethyl acetate / hexanes. The product was recovered as a white solid in 63% yield. m.p. 129.degree.-131.degree. C.

example b

2-Chloro-6-(trimethylsilyl)benzoyl chloride

The compound of Example a (2.4 g, 0.01 mol), thionyl chloride (3.57 g, 0.03 mol), toluene (50 mL), and 1 drop of DMF were stirred at RT overnight. The reaction mixture was twice concentrated under vacuum from toluene (50 mL) to afford the desired product as a brown oil in 100% yield.

example c

2-Bromo-6-(trimethylsilyl)benzoic acid

2-Bromobenzoic acid (30.15 g, 150 mmol), THF (400 mL), and diisopropyl amine (33.4 g, 330 mmol) were stirred under nitrogen and cooled to -78.degree. C. 10M n-BuLi in hexanes (31 mL, 0.31 mol) was then added dropwise, followed by the dropwise addition of TMSCl (17.4 g, 160 mmol). The mixture was allowed to slowly warm to -30.degree. C., stirred for 1 h, then was poured into 25% citric acid (100 mL) and stirred for 15 min. The mixture was extracted with two 100 mL portions of ether, which were combined and washed three times with sat aq NaHCO.sub.3 solution. The bicarbonate solution was acidified with 25% citric acid and extracted with three 100 mL portions of ether. These extracts were combined, dried (MgSO.sub.4), and concentrated. The crude product was purified by recrystallization from ether / hexanes, and the desired product was recovered as a white solid in 35% yield. m.p. 139.degree.-141.degree. C.

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Abstract

A method of controlling Take-All disease of plants by applying a fungicide of the formula wherein Z1 and Z2 are C and are part of an aromatic ring which is [benzothiophene]thiophene; and A is [selected from] -C(X)-amine [wherein the amine is an unsubstituted, monosubstituted or disubstituted amino radical]wherein the amine is a monosubstituted or a disubstituted amine, wherein one of the substituents has a cyclic moiety, said cyclic moiety which is chosen from the group consisting of thienyl, furanyl, and a non-heterocyclic substituent, wherein when the amine is disubstituted, the second substituent is a non-cyclic substituent, -C(O)-SR3, -NH-C(X)R4, [and] or -C(=NR3)-XR7; B is -Wm-Q(R2)3 or selected from [O-tolyl]o-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R4; Q is C, Si, Ge, or Sn; W is -C(R3)pH(2-p)-; or when Q is C, W is selected from [-C(R3)pH(2-p),[-C(R3)pH(2-p)-, -N(R3)mH(1-m)-, [-S(O)p-,] -S(O)p-, and -O-, X is [0] O or S; n is [0, 1, 2, or 3]2; m is 0 or 1; p is 0, 1, or 2; wherein the two R groups are combined with the thiophene ring to form a fused ring which is benzothiophene; each R and R2 is independently defined herein; R3 is C1-C4 alkyl; R4 is C1-C4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino; and R7 is C1-C4 alkyl, haloalkyl, or phenyl, optionally substituted with halo, nitro, or R4; or an agronomic salt thereof.

Description

FIELD OF THE INVENTIONThis invention relates to a method for the control of Take-All disease in plants, particularly cereals, by the use of certain substituted aryl compounds, some of which are novel, and fungicidal compositions for carrying out the method.BACKGROUND OF THE INVENTIONTake-All disease is a serious problem in the production of cereals, particularly wheat and barley. It is caused by the soil-borne fungus Gaeumannomyces graminis (Gg). The fungus infects the roots of the plant, and grows throughout the root tissue, causing a black rot. The growth of the fungus in the roots and lower stem prevents the plant from obtaining sufficient water and / or nutrients from the soil, and is manifested as poor plant vigor and, in severe instances of disease, by the formation of "whiteheads," which are barren or contain few, shriveled grains. Yield losses result. Gaeumannomyces species also infect other cereal crops, for example, rice and oats; and turf.Currently the primary means of avoi...

Claims

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Application Information

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IPC IPC(8): A01N37/18A01N41/00A01N37/40A01N37/26A01N37/44A01N41/10A01N37/36A01N55/02A01N55/04A01N55/00C07C317/00C07C237/00C07C233/69C07C237/30C07C235/60C07C317/44C07C235/00C07C233/00C07C233/65C07C233/66C07C323/60C07C323/00C07F15/00C07F15/02C07F7/00C07F7/30C07F7/22C07F7/08A01N43/10A01N43/36A01N43/40A01N55/10A61K31/165A61K31/38A61K31/405A61K31/41A61K31/415A61K31/47A61K31/555A61K31/695C07D209/02C07D215/38C07D249/08C07D409/04C07F7/04
CPCA01N37/18A01N37/26A01N37/40A01N37/44A01N41/10A01N55/00A01N55/02A01N55/04C07C233/65C07C233/66C07C233/69C07C235/60C07C237/30C07C317/44C07C323/60C07F7/0812C07F7/0814C07F7/0818C07F7/2212C07F7/30C07F15/025C07C2101/04C07C2101/08C07C2601/04C07C2601/08C07F7/081C07F7/2208
Inventor PHILLION, DENNIS P.BRACCOLINO, DIANE S.GRANETO, MATTHEW J.PHILLIPS, WENDELL G.VAN SANT, KAREY A.WALKER, DANIEL M.WONG, SAI C.
Owner MONSANTO TECH LLC
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