Pest controlling agent

专利摘要:
Imidazole derivs. of formula (I) and thier salts with bases are new: (where CXYZ represents a C atom with 3 bonds attached to heteroatoms).
公开号:SU793356A3
申请号:SU772455516
申请日:1977-03-02
公开日:1980-12-30
发明作者:Бекк Гунтер；Зассе Клаус；Хейтцер Гельмут；Ойе Лудвиг；Шмидт Роберт；Шейнпфлуг Ганс；Хамманн Ингеборг；Брандес Вильгельм
申请人:Байер Аг (Фирма)；
IPC主号:

专利说明:

one
This invention relates to chemical means of plant Söshts1t based on an active agent.
Insecticides and acaricides are known, the active principle of which are halogen-substituted imidazole derivatives, for example, 1-ethylthiomethyl-2.4. / 5-tribromimidazole I.
However, the known insectoacaricides are not sufficiently active.
It is also known that preparations whose active ingredient is benzimidazole-2-carboxylic acid derivatives are used as herbicides 2.
However, these herbicides are not active at low concentrations.
The aim of the invention is to find HOBbht plant protection products with high biological activity.
This goal is achieved by the use of chemical plant protection products, the active principle of which are 4,5-dichloroimidazole derivatives of the general formula.
irl /
sDtsLs-t
W, n g
where X, Y and Z are, independently of each other, the fluorine or sodium salt of this compound, methyl mercapto, chlorophenoxy; .
5 X, Y and 2, together with the adjacent carbon atom, form a C5M group or the corresponding sodium, triethylammonium, butylammonium, N, M-dimethyl-benzyl-ammonium, dibutyl 10 ammonium, morpholinium tris- (2oxy-ethyl 1 ammonia).
if X and Y together denote oxygen, then Z is methyl mercapto or ratS dicyl -0-R, where R is C-C-alkyl, substituted by methoxy, bromine, phenyl, cyclohexyl, or the radical is Nl, where is hydrogen, alkyl or together with the nitrogen atom radikgshy R
20. form pyrrole, piporidine, or an divaro-JSr-Bj ft ,, - ALKIL
25 or the corresponding sodium salt, benzyl, or the radical is NHR, where R "is C -, - Se-alkyl, cyclohexyl, benzyl, phenyl, fixed with chlorine, fluorine methyl ethyl, trifluoromethyl, nitrocryopic, difluoromethyl, trifluoromethoxy, trifluoromethylmeptanepticentropt-dipropthechroptonechne-crystalline scptone , chlorofluoromethyldifluoromethoxy or the group O V or the radical -NoC-MJRj, where Cn is; if X and Y together mean Z — NH —rpynna or X, Y, and Z mean together with the adjacent carbon atom where Rf is the radical —c with I-B5 tert-butyl, phenyl substituted by chloro bromine, methyl, trifluoromethyl, trifluoromethylcapto, trifluoromethoxy or X, Y and Z together with the adjacent carbon atom form the phenyl radical f p 6,. replaceable with chlorine, trifluoromethyl, or X, Y and Z together mean benzoxazole, dichloroisothiazole oxadiazole, aminothiadiazole, triazolone. The content of the active substance in the agent is from 0.1 to 96% by weight. The proposed compounds were prepared with 1) 4,5 dichloro-2-dichloromethylene-imidaeol of formula (&). or 4,5-di chloro-2-trichloromethyl-imidazole form (til) or dimeric ketene 4,5-dichloro-imidazole-2-carboxylic acids of the formula {IV) .U) Cl-k. . Cl-J is reacted with nucleophiles, of the general formula H-Z, with Z being as defined above; 2) compounds of the formulas Ci-j-ji ei-IN Q} - Ttf ci-Sf} OP -., HH are reacted with nucleophiles of the general formula (with R having the above values; 3) nitrile 4,5-dichloroimidazole- 2 carboxylic acid is reacted with nucleophiles of the general formula I HZ, with Z being as defined above; 4) 4,5-dichloro-imidazole-2-thiocarboxylic acid amide is reacted with alkylating agents and the reaction products are additionally hydrolyzed or cyclic; 5) imidchloride of the general formula - t - N C1 J N - A. Wherein aryl is an aryl radical, it is reacted with compounds of the general formula Z-H, wherein Z is as defined above; 6) imidchloride of the general formula (hydrolyzed in the presence of diluents; 7) 4,5-dichloro-2-dichloromethylenimidazole of the general formula (I) is reacted with equimolar amounts of the amine of the general formula (y). Anti-pest agents based on active agents obtained have a wide range of effects. They can be applied both before and after the emergence of shoots. They are suitable for weed control in cereal crops, cotton and corn fields as selective herbicides and, with higher amounts of active ingredient, can be used as retinal herbicides. The proposed agents have strong fungitoxic and bacteriotoxic effects. At concentrations necessary for the control of fungi and bacteria, they do not harm cultivated plants. For this reason, they are suitable for use as a plant protection agent for controlling fungus and bacteria. The proposed agents have a wide range of action and can be applied against fungal parasites that infect above-ground parts of plants or infect plants from the soil, as well as against seed-borne pathogens. They are especially effective if they are used as a seed preparation or a soil treatment agent against phytopathogenic fungi sticking to the OR seed seeds in the soil and causing them. seedlings, root rot, trachyomics: and seed diseases are also used to control insects. Forms of application of conventional solutions, emulsions, suspensions, powders, pastes, granules. They are prepared by methods common in the manufacture of preparative forms of pesticides.
In this way, the compounds listed in Table 2 are obtained. 1-9.
Example. Post-emergence application.
Solvent - 5 weight.h. acetone, emulsifier .- 1 weight.h. alkyl aryl polyglycol ether.
To obtain a preparation based on the active principle, 1 weight.h. it is mixed with the indicated amount of solvent, the indicated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Experimental plants, having a height of 5-15 cm, are sprayed with this preparation using the indicated in table. 10 the number of active beginning (per unit area). The concentration of the drug is chosen so that in 2000 liters of water per 1 ha contained are listed in the table. 10 the number of active principles. After three weeks, the degree of damage to the plants in points was determined compared to the development of untreated control plants. In this case, 1 means 100% action, 3 means very good, a neck, 5 means moderate, 9 means no effect (as with untreated controls).
PRI mme R 2. Pre-emergence application.
Solvent - 5 weight.h. acetone, emulsifier - 1 weight.h. alkyl aryl polyglycol ether.
To obtain a preparation based on the active principle, 1 weight.h. it is mixed with the indicated amount of solvent, the indicated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Seeds of experimental plants / sown in the soil and after 24 hours, watered with the preparation of the active principle. The amount of water for irrigation per unit area is kept constant. After three weeks, the degree of damage to the plants is determined in points compared with the development of untreated control plants.
The results are shown in table. 11P r i me R 3. Protective action against grain rust.
To prepare a preparation based on an active start of 0.25 weight. H, it is dissolved in 25 wt.%. dimethylformamide and 0.06 weight.h. alkyl aryl polyglycol ether and 975 parts by weight added. water. The preparation is diluted with water to the desired concentration, obtaining a spray liquid.
To test the strength of the protective effect, young single-leaved plants of wheat varieties Michigan Amber are inoculated with a suspension of Puccini and Recondita uredospores in 0.1% water agar. After drying the suspension.
The spores of a wheat plant are sprayed to a moisture content of dew with prepared liquid, and placed for incubation for 24 hours in a greenhouse — at a temperature of 20 s and air humidity of 80–90%.
After 10 days, the degree of damage to plant leaves by rust pustules is determined by the nine-point system, with 1 indicating 100% effect, 3- very good action, 5 - moderate and 9 - low action.
0
Data on the conditions and results of the experiments are given in Table. 12.
PRI me R 4. Experience with the growth of the mycelium.
Used nutrient medium
5 parts by weight:
Agar-agar20
Potato decoction 200 Malt5
Dextrose15
Peptone5
0
Nag HP 042
Sa (MOZ) 20.3
The ratio of the mixture of solvents and nutrient medium: 2 weight.h. solvent mixture: 100 weight.h. agar nutrient medium.
The composition of the solvent mixture, parts by weight: Dimethylformamide or acetone 0.19 Emulsifiers. (Alkylarylpo-0.01 liglycol ether) Water 1.80
To obtain the desired concentration of the active principle in the nutrient medium, the amount of the active ingredient is mixed with 2 parts by weight. solvent mixtures. Concentrate s the above ratio is thoroughly mixed with liquid to a nutrient medium and poured into Petri dishes with a diameter of 9 cm.
At the same time, control plates without the preparation were set.
After cooling and solidification of the nutrient medium, the plates are inoculated with the following table. 13 types of fungi and incubated at temperature.
The assessment is carried out as the growth rate of the fungi after 4 to 10 days. In the assessment, the radial growth of the mycelium on the treated nutrient media is compared with the growth on the control nutrient media in a nine-point system: 1 - no growth of fungi; up to 3 - growth retardation is very strong,
up to 5 - average growth rate {up to 7 - weak growth delay; 9 - the growth is the same with the untreated control.
Active principles, their concentrations and results of experiments are given.
in tab. 13.
Example 5. Experience with larvae P haedon. Solvent 3 weight.h. Mamida dimethylformer, emulsifier - 1 weight.h. alkyl aryl polyglycol ether. For the preparation of the active ingredient, 1 weight, h. it is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. The drug of the beginning of the beginning is sprayed with cabbage leaves (Brass le olevacea) before Dropsing and the larvae of the horse beetle (Phaedon cochleagiae) are planted on them. After three days, the degree of sacrifice in percent is determined at that, 100% means that all the larvae are euthanized, and 0% means that not one larva has been euthanized. The active principles, their concentrations, the time of assessment and the results are given in Table. 14. PRI me R 6. Experience with the larvae of the cabbage moth. Solvent - 3 weight.h. dimethylformamide, emulsifier - 1 weight.h. alkyl aryl polyglycol ether. In order to obtain a preparation of the beginning of 1 wt.h. it is mixed with the specified amounts of diluent and emulsifier, and diluted with water to the desired concentration. The active ingredient is sprayed with cabbage leaves (Brassic oleracea) before dropping and the cabbage moth larvae (Plutella magulipennts) are planted on them. At the end of the 3rd day, a certain degree of killing is expressed as a percentage, in addition, 100% means that all the larvae are euthanized, 0% - not one larva has been euthanized. The active principles, their concentrations, time of assessment and the results are shown in Table. 15. Example Experience with Tetranychu (steady). Solvent - 3 weight.h. acetone, emulsifier 1 weight.h. alkyl aryl polyglycol ether. to obtain a 0.1% active drug, 1 part of it is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water. The preparation is sprayed before the formation of droplet bean plants (Phasealus vulgaris), which are severely affected by the spider mite (Tetra nychus urtlcae) at all stages of growth. When 2 days have passed, the degree of killing is determined in percent; 100% means everything. ticks are killed, and 0% - not one tick is not killed. The active principles, their concentrations, and the results of the experiments are given in Table. 16. Example. Experience with Phycophtora (Tomatoes). Protective action. Solvent: 4.7 weight.h. aceton; emulsifier; 0.3 weight.h. alkyl aryl polyglycol ether; water 95 hours. To obtain a 0.0025% con. the concentration of active ingredient is mixed with the indicated amount of solvent and diluted. The concentrate is filled with water containing these additives. Young tomato plants in a stage from 2 to 4 leaves are sprayed with the preparation before dropping. For 24 hours, the plants are left to stand in a greenhouse with a relative humidity of 70%. The plants are then inoculated with an aqueous suspension of Phytophtora iniestoins spores, and placed in a humid chamber with 100% atmospheric humidity and a temperature of 18-20 ° C. After five days, the percentage of damage to tomato plants is determined: 0% means no damage, 100% means all plants are completely affected. The results are given in table. 17. EXAMPLE 9. Test with growth of mycelium. Nutrient medium used, parts by weight: Agar-agar 20.0 Potato decoction 200 Solod5, O Dextrose 15.0 Peptone 5.0 NaoHP042.0 Ca (N02,) 20.3 Mixture ratio of solvents and nutrient medium: 2 parts by weight solvent mixture: 100 weight.h. agar nutrient medium. The composition of the solvent mixture, wt.h; Dimethylformamide 0.19 Emulsifier (alkylaryl polyglycol ether) 0.01 Water 1.80 To obtain a concentration of the active principle in a nutrient medium 10 ppm. The required amount of active principle is mixed with 2 parts by weight. solvent mixtures. The concentrate in the specified ratio is thoroughly mixed with liquid nutrient medium cooled to 42 ° C and B11 is poured into Petri dishes with a diameter of 9 cm. At the same time, control plates are placed without the preparation. After cooling and solidification of the nutrient medium, the plates are inoculated with various types of fungi and bacteria and incubated at 21 ° C. The evaluation is carried out as the growth rate of the organisms after
4-10 days. When evaluating, compare radial growth on treated nutrient media with growth on control nutrient coned.
The test is carried out in points
0 - no growth
1- very strong growth retardation
2- average growth retardation;
3- weak growth retardation,
4 - growth is the same with the untreated control.
The active principles, their concentrations and results are visible from the table. 18.
I'll try it on. Experience with the treatment of shoots (bread rust). Protective action (destroying the leaves of mycoses).
For the preparation of the active drug start 0.25 weight.h. it is absorbed by 25 parts dimethylformamide and 0.56 weight.h. alkyl aryl polyglycol ether and add 975 wt. water. The concentrate is diluted with water to the desired concentration of spray liquid.
To test the protective effect of young single leaf plants
Michigan Amber wheat is inoculated with a suspension of Pucctnia recondita uredospore in 0.1% water agar. After the spore suspension is dried, the wheat plants are sprayed to J with the dew moisture of the prepared liquid and placed for incubation for 24 hours in a greenhouse at a temperature and 100% humidity. After 10 days of staying-Q, neither plants at and humidity
 air from 80 to 90% determine the damage to plants by rust pustules. The degree of damage is expressed as a percentage of the untreated control plants. At the same time, 0% means no damage, 100% damage is the same as in the control. The less rust damage, the more effective the active principle,
Active principles (concentrations
20 of them in the spray liquid (0.025 wt.%) And the extent of the lesion are visible from table. nineteen.
Thus, the proposed compounds have high biological activity.
T b face
methylimidazole
4-, 5-Dichloro-2-tris- (methyl mercapto) omethylimide 3ol
4,5-Dichloro-2-tris- (4-chlorophenoxy) me. Methylimidazole
4,5-Dichlorimidazole-2-thiocarboxylic acid S-methyl ester
4,5-Dichlorimidazole-2-thiocarboxylic acid amide
4,5-Dichloroimidazolitrile
4,5-dichloroimidazolitrile sodium salt
Triethylammonium salt of 4,5-dichloroimidolitrile
4,5-dichloroimidazolitrile butyl ammonium salt
m, N-dimethyl-benzyl-ammonium salt of 4,5-dichloroimidazolitrile
4,5-dichloroimidazolitrile dibutylammonium salt
Morpholini salt 4,5-d chlorimidazolitrile.
175-177 220-222 162-169
171-173 187-189 -250®
X
38-40
1 2-124
90-92
56-58
144-146
eleven
79335612
Tris- {2-hydroxy-ethyl) -ammonium salt of 4,5-dichloroimidazolitrile
2- (4, 3 D divsorimidazolyl- (2) -be Neeksazol 196-198
2- (4,5-Dichlorimidazolyl (2) -oxadiazolyl {2) -3,4-dichloroisothiazole266
2- {4,5-Dichlorimvdazolide- (2) -5 amino-1 3, 4-thiadiazole i147
2- (4,5-Dichlorimidazoline- (2) -1,2 / 4-triazolone (5); 176-178
WITH
SNS
SNS
SNA
CHg-CH -O-CgHj
CH -CH-O-CH -CH -OCH
-SNg-CGH-CT
Continued table. one
102
Table 2
C1- | - W about C1xCg / СQR
131 150
70
Oil 119 163
180 formulas.
Compound total
CHj
-T (cH2-cH2-CHjL
36 37
-about
Table 3
ci-y-: N ° n o
hexane)
93 petroleum ether
242 (dioxane)
Compounds of general formula. (j
T a B L I C a 4
SSS
C-W-R About General Formula H
SNS
-Sya
SVZ
si
-snS
No.
CHj-CHj-CH
IT a b l and c a 5
C1-g-W
C1 Cr-Tom n g
146,140
cn
-C-CH; y218
SNS SNZ
c-CgH5153
CH5
Continuation of table.5
51
-Syag52 01
53
se
54
se
186
172
244,206
265 (toluene)
74
W - / -SCFjCl 244 (acetonitrile)
75
Continued table. five
QCf 205 (acetonitrile)
76
215 (glyconitrile)
Cl
Cl
OCTj 254 (acetonitrile)
.CTj
290 (dioxane)
About OST) 202 (acetonitrile)
211 (acetonitrile)
nineteen
83
OCF.J-CHC1F 202 (acetonitrile;
oht
84
 F
79335620
Continued tabl, 5
218 (acetonitrile)
85
290
of the general formula p, P j | s-TSH- -TOI-R
General formulaI In ,, ,,
Compounds of general formula
Table b Cl-nn
Cl-tj-
ai
but oh
.table 7
C1-1G C1
01- C N-H. n
Table 8
C1-tr N
11 HTS-N
88
212
R
 compounds
C1
CP,
C1
// VCF,
, Br
WITH
CHj
/ Vci .a
C1
/ Vce
CF Cl Cl
i
C1
Continued table. eight
Mp, ° C
204 (toluene)
210 (acetonitrile)
CTj 212 (toluene)
  285 (acetonitrile)
210 (acetonitrile)
242 (chlorobenzene)
240 (chlorobenzene)
255 (chlorobenzene)
127 (cyclohexane)
229 (chlorobenzene)
242 (acetonitrile)
SCFj;
SCIj 253 (acetonitrile)
216 (acetonitrile)
Compounds of the general formula Ct-s, -C "And
.CTs
103
104
 212 (acetonitrile)
105 - /
Cl
lae
Cl
SG
107
CTj
Cl 108
v ycTi or
 Cl
09
Cl
250 (adonitrile
ten
Cl dioxane)
Cl
182 (acetonitrile) 11
Cl Cl
200. (acetonitrile)
12
OCTj
T a b. Ji and c 9
"T-to-and
H
205 (acetonitrile)
192 (acetonitrile) CH1LSH1PSHG R01L L 4f
inin "" n4ninfOt-t -IO in in h cn tn in tn in in tn in 1 in inin ininininincnintninininmi /) inininininininininininro inintnirttnin TroMroinmin
inininminminintNCNininr in inin inin in in n inm
minininminininminininjroi in in-n in in-ff} r "t
in in in
in about “HO t-t about
ee tn
f
in n

in t
tN about V CS rn tS
N in in 4in. in
II
in in in in
in about
in
in about
in about
"
about
in chON
00
n
CM) GMP cv n n GO MCS M ininmininmin -) inininin -rofMinininin Jinninininin GO in CO in in v v fo fo fM-w fo
HsaecTHO
Table.12 999 99 (known) 22
Continued table. 12
Table 1 9: 995 9S- -9
Continued table. 13
35
Continued table. 15
CHs-NH-C-s CNH-shh -s-
I
(known) 57
64 67
71
36
793356
Table
sixteen
| Degree killing Compound,%
n yVo-o-NlcHj)
Kyi
XCHS) ;,
8100
7199
6590
7698
9090
8799
T a b l and c a 17
56
12
four
55
58
87
61
59
63
91
65
70
92
96
54
54
98
76
78
79
100
81
84
108
109
Table 18
about
- 1 - 1 21315
511 - 5-5

55-1
- 5 5 53
5151
1 1 - 1535
1155
11-2
1315

权利要求:
Claims (1)
[1]
SUMMARY OF THE INVENTION A pest control agent containing an active ingredient and an additive selected from the group of solvent, surface active agent, solid carrier, characterized in that, in order to increase the biological activity, it contains 4,5-dichlorimideaol derivatives of the formula
VNIIIPI
Order 9625/67 or phenol radical;
if X and then the Z-NH ^ group, or X, Y and Z, together with an adjacent atom of the genus a radical, where Rg is tert-butyl, phenyl substituted with chlorine, bromine, methyl, trifluoromethyl, trifluoromethyl mercapto, trifluoromethoxy or X, Y and Z together with the adjacent carbon atom form the radical -dsN-Rg, where Rg is phenyl substituted with chlorine, trifluoromethyl or X, Y and Z together. They mean benzoxazole, dichlorioethiazoloxadiazole, aminothiadiazole, triazolone, and the content of the active substance in the agent is from 0.1 up to 95 wt.%, the rest is additive.

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同族专利:

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公开号 | 公开日

---

ZA771480B|1978-02-22|

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DE2610527A1|1977-09-29|

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引用文献:

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公开号 | 申请日 | 公开日 | 申请人 | 专利标题

---

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US4314844A|1979-01-11|1982-02-09|Rohm And Haas Company|Herbicidal substituted imidazoles|

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DE2901862A1|1979-01-18|1980-07-31|Bayer Ag|4,5-DICHLORIMIDAZOLE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS HERBICIDES|

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DE3104759A1|1981-02-11|1982-08-19|Bayer Ag, 5090 Leverkusen|DIHALOGENATED IMIDAZOLIC CARBONIC ACID AMIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS HERBICIDES|

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CA1339133C|1987-03-13|1997-07-29|Rikuo Nasu|Imidazole compounds and biocidal composition comprising the same for controlling harmful organisms|

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DE4017338A1|1990-05-30|1991-12-05|Bayer Ag|SULFONYLATED CARBONIC ACID AMIDES|

法律状态:

优先权:

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申请号 | 申请日 | 专利标题

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DE19762610527|DE2610527A1|1976-03-12|1976-03-12|-Dichloro-imidazole -carboxylic acid derivs. - useful as herbicides, fungicides, bactericides, insecticides etc.|

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