DD209716A1 - FUNGICIDAL AGENT (I) - Google Patents

Abstract

The invention relates to novel fungicidal compositions which, in addition to the usual auxiliaries and tracer substances, contain delta, delta-dihaloacetophenones of the general formula in which R 1, R 1, chlorine, bromine, R 2, hydrogen, nitro, bromine, chlorine, alkyl , Cyan and n are the numbers 1 to 3. Excluded from this general formula are 4-chloro-3-nitro- and 2-chloro-3-nitro-omega, omega-dihaloacetophenones.

Description

242506 6

VEB CHBMIEKOMBHfAT BITTSEPELD 2206

Fungicidal agent (I)

Field of application of the invention

The invention relates to fungicidal α , <.:> -Dihalogenaoetophenone for controlling fungal diseases on crop plants.

Characteristic of the known

For combating fungal diseases on crops known to a wide extent organometallic compounds of Äthyl-bis-dithiocarbamic acid, z. For example, Maneb (U.S. Patent 2,504,404, U.S. Patent 2,710,822), Mancozeb (U.S. Patent 2,504,404, Belgian Patent 996,264), and Sineb (U.S. Patent 2,457,674).

Of great importance as fungicides are in addition to the metal salts of dimethyldithiocarbamic the thiuram derivatives, eg. B. The Tetramethylthiuramdisulfid (US Patent 1 972 961) · Sin Fachsteil the metal salts of the ethylene-bis-dithiocarbamidsäure is that they act on crops phytotoxic. Furthermore, the organometallic compounds of ethylene-bis-dithiocarbamic acid have, in addition to a good action against Phytophthora infestans, only a mediocre action.

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Pusarimn culmoruia, Botrytis aea and Alterna.ria tenuis. On the other hand, tetrarnethyl thiuram disulfide has a very good action against Botrytis cinerea. However, the effect on Phytophthora infestans is not satisfactory with correspondingly low expenditure amounts.

JP-PS 7 021 297 and DD-PS 92 602 describe the fungicidal action of ui- halogenated acetophenones. However, the compounds listed therein show only an average action against Phytophthora infestans, Pusarium culmorurn, Botrytis cinerea and Alternaria tenuis.

Aim of the invention;

The aim of the invention is to develop new fungicidal agents for the inhibition of fungal diseases on crop plants having a broad spectrum of activity.

^ _R Dar interpretation of the invention vVe.sens

The object is achieved in accordance daj3 the new fungicidal agents in addition to the usual excipients and Trägerstofi'en 'compounds of the general formula

chlorine, bromine, Hp hydrogen, nitro, chlorine, Brora, alkyl, cyano and η are the numbers 1 to 3, contained in the Ii.

Excluded from this general formula are 4-chloro-3-nitro- and 2-chloro-3-nitro-cJ, cJ-dihaloacetophenones.

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The invention u? _f cJ-Dihalogenacetophenone show a higher fungicidal activity than the above-mentioned generally known commercial preparations · The active compounds according to the invention are in contrast to the organometallic compounds and the thiuram derivatives, for. B, maneb and tetramethylthiuram disulfide, both against Phytophthora infestans as well as Fusarium culmorum, Botrytis oinerea and Alternaria tenuis highly effective and have a significantly stronger fungicidal activity than previously known fungicidally active (J-Halogenaoetophenone ·

The LJ j ύ) -Dihalogenacetophenone can sioh by known methods z. B. by halogenation of acetophenones (DE-AS 1 231 233, GB-PS 1 062 369) or by peace l _y Gr sfts acylation with acid chlorides produce (DE-OS 1 768 624).

Following these procedures, the following (j, υ) dihaloacetophenones listed in Table 1 were synthesized and tested for their fungicidal activity:

Table 1

ü _s O -dihaloacetophenones "V 0 • C-CHRR. 1 R ₂ Fp ( ⁰ G) I τ? / Γ e > 1 4-Gl 83 to 83.5 V ⁵ E ₂ (V = Cl br 4-Br 92-94 connection br br H 1 br br 4-Cl 93.5 to 94.5 1.6105 2 br br 4,5-Cl 61-63 3 Cl Cl 2-HO ₂ ; 4,5-Gl 86-88 4 Cl Cl 3-M) ₂ y 4-Cl 54-56.5 5 Cl br 4,5-Cl 58 6 Cl br 7 ! 8th

) UO 0 - 4 - 4-Br 2206 V ⁵ connection β ^H 1 Pp ( ⁰ C) 1.6052 9 Cl br 4-NO ₂ 4-Br 10 Cl Cl 3-FO ₂ 57-58 11 Cl Cl 3-IK) ₂ J 5-Br 66-68 12 egg br 4-Br 80-82 13 Cl br 3-KO ₂ J 63 1.5798 14 Cl egg 2,4-Cl 15 Cl Cl 2-NO ₂ j 5-NO ₂ 104 1.6235 16 br br 3-NO ₂ 17 br br 2-NO ₂ 56-59 1.6075 , 18 br br 4,5-CH ₃ 19 Cl Cl 2,4-CLJ 82-85

The active compounds according to the invention can be converted into the customary formulations, such as emulsifiable concentrates, wettable powders, pastes and granules. Lie formulations are prepared in a known manner, for example by vermisohen the active compounds with Streokmitteln, such as liquid solvents and / or solid carriers, optionally with the use of surfactants, such as emulsifiers and / or dispersants

In the case of using water as an extender z. B, also organic Jjb'sungsmittel be used ·

Suitable solid carriers are ground natural minerals, such as silicic acid and silicates, in question.

Nonionic and anionic emulsifiers and, as dispersants, sulphite liquors and methyl cellulose are mentioned as emulsifiers.

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example 1 In vivo test

Tomato plants (Ijyoopersicum aseulentum) are treated with 0.1 $ strength and 0.01% strength spray liquor, supplied while drying of the coating compositions is infected with the test fungus Phytophthora infestans * The plants are then kept at 20 ⁰ C and relative humidity 96 #. Hach 48 hours incubation period, the infected plants continue to develop under normal greenhouse conditions, The evaluation is carried out after 6 days by assessing the pro zentualen Blattbefalls with the fungus parasite pathogens · The infestation is detected in the following Boniturnoten

1 = no control success

2 = low control success

3 - average control success

4 ^s good control success

Table 2 Concentration W infestans BekämpfungserfοIg Combatants succeed Phytophthora 0.1 0.01 1 Active substance (compound Er.) 4 3 untreated contro He 0.1 0.01 maneb 0.1 0.01 4 1 4, O, ü -Trichlor- 3.7 1 3-nitroacetophenone (known) 4-nitro-O-bromo-acetophenone (known)

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Active ingredient (compound / Mr ») Concentration 00 BekämpfungserfοIg , 2 ... 0.1 0.01 4 4 3 0.1 0.01 4 4 4 0.1 0.01 4 4 5 0.1 0.01 4 2,3 9 0 * 01 4 3 10 0.1 0.01 4 1 12 0.1 0.01 4 4 13 0.1 0.01 4 2,7 16 0.1 0.01 4 3.3 17 0.1 0.01 4 4 18 0.1 0.01 4 4

BeisOiel 2

In vitro test

The test fungi are inoculated on agar plates containing drug concentrations of 0.1 #, 0.01 #, and 0.001 % . Evaluation takes place after 10 days by evaluation of fungal growth. · Growth is recorded according to the following rating values:

1 * no growth inhibition

2 * »weak growth inhibition

3 = strong growth inhibition

4 ^a complete growth inhibition

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Table ß from Alternaria tenure · Botrytis cinerea Alternaria tenuis growth inhibition and, Pu, sari τχυ \ <ji i7winrum 1 1 $ otrvtis c errrere a Concentration C *) Pusarium eulmorujn 4 4 4 4 4 3 Active ingredient (compound 2fr «) - 1 4 1 1 4 3 1 untreated control 0.1 0.01 0.001 4 4 3 4 4 1 4 4 1 Tetramethylthitiram disulfide 0.1 0.01 0.001 4 4 1 4 4 4 4 4 4 4, O .cJ-tri-chloro-3-nitroaoetophenone (known) 0.1 0.01 0.001 4 4 1 4 4 4 4 4 4-Nital-i-bromo-aoetophenone (known) 0.1 0.01 0.001 4 4 4 4 4 4 4 4 4 1 0.1 0.01 0.001 4 4 4 4 1 4 4 1 2 0.1 0.01 0.001 4 4 4 4 4 1 4 4 1 3 0.1 0.01 0.001 4 4 1 4 4 4 4 4 4 4 0.1 0.01 0.001 4 4 1 4 4 4 4 4 4 5 0.1 0.01 0.001 4 4 4 y,. , 4 4 1 4 4 1 8th 0.1 .. '. ^; .:.; ^ κΐν- 0,01 0,001 .'W " ': 4 4 1 4 4 1 9 0.1 0.01 0.001 4 4 1 10 0.1 0.01 0.001 4 4 1 11

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Active substance Concentration Fusarium Botrytis Alternaria (Compound No.) (#) oulmorum cinerea tenuis

0.1 0.01 0.001 4 4 4 4 4 4 4 4 4 0.1 0.01 0.001 4 4 4 4 4 4 4 4 4 0.1 0.01 0.001 4 4 1 4 4 1 4 4 1 0.1 0.01 x 0.001 4 4 4 4 4 3 4 4 3 0.1 0.01 0.001 4 4 4 4 4 4 4 4 4 0.1 0.01 0.001 4 4 4 4 4 4 4 4 4 0.1 0.01 0.001 4 4 4 4 4 4 4 4 4 0.1 0.01 0.001 4 4 1 4 4 1 4 4 1

Claims (1)

242 5 06 θ - * - ²² ° ⁶ Brfindung say spru ooh Fungicidal agents, characterized in that they in addition to übliohen excipients and carriers as active substances compounds of the general formula in which H, E _{1 is} chlorine, bromine, R _{2 is} hydrogen, UTitro, bromine, chlorine, alkyl, cyano and η are the numbers 1 to 3, contain "4-chloro-3-nitro and 2 excluded from this general formula -Chlor ~ 3-nitro- <J, tJ-dihalogenaoe.tophenone _#