IL30933A - Pesticidal preparations containing benzimidazole compounds and new benzimidazole compounds - Google Patents
Pesticidal preparations containing benzimidazole compounds and new benzimidazole compoundsInfo
- Publication number
- IL30933A IL30933A IL30933A IL3093368A IL30933A IL 30933 A IL30933 A IL 30933A IL 30933 A IL30933 A IL 30933A IL 3093368 A IL3093368 A IL 3093368A IL 30933 A IL30933 A IL 30933A
- Authority
- IL
- Israel
- Prior art keywords
- lower alkyl
- formula
- phenyl
- preparations
- compound
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 21
- 230000000361 pesticidal effect Effects 0.000 title claims description 5
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 230000002363 herbicidal effect Effects 0.000 claims description 7
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 6
- 150000001556 benzimidazoles Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- -1 benzimidazole compound Chemical class 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 230000000855 fungicidal effect Effects 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 231100000194 ovacidal Toxicity 0.000 claims description 3
- 230000003151 ovacidal effect Effects 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000000853 adhesive Substances 0.000 claims description 2
- 230000001070 adhesive effect Effects 0.000 claims description 2
- 239000002270 dispersing agent Substances 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000005059 halophenyl group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000006501 nitrophenyl group Chemical group 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 241000607479 Yersinia pestis Species 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000000575 pesticide Substances 0.000 claims 1
- 239000002562 thickening agent Substances 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 239000003921 oil Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- NOGORYGYLODPPL-UHFFFAOYSA-N o-methyl methanethioate Chemical compound COC=S NOGORYGYLODPPL-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003673 urethanes Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GBDZXPJXOMHESU-UHFFFAOYSA-N 1,2,3,4-tetrachlorobenzene Chemical class ClC1=CC=C(Cl)C(Cl)=C1Cl GBDZXPJXOMHESU-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 241000219318 Amaranthus Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 235000011331 Brassica Nutrition 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 240000005250 Chrysanthemum indicum Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 235000017896 Digitaria Nutrition 0.000 description 1
- 241001303487 Digitaria <clam> Species 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241000237858 Gastropoda Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 101100400378 Mus musculus Marveld2 gene Proteins 0.000 description 1
- OKOVSTKGUBOSTB-UHFFFAOYSA-N N-(1H-benzimidazol-2-yl)carbamic acid ethyl ester Chemical class C1=CC=C2NC(NC(=O)OCC)=NC2=C1 OKOVSTKGUBOSTB-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- WREOTYWODABZMH-DTZQCDIJSA-N [[(2r,3s,4r,5r)-3,4-dihydroxy-5-[2-oxo-4-(2-phenylethoxyamino)pyrimidin-1-yl]oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]1N(C=C\1)C(=O)NC/1=N\OCCC1=CC=CC=C1 WREOTYWODABZMH-DTZQCDIJSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
The present invention provides pesticidal preparations as active at least one compound of the general I 0 wherein and are the same or different and are each or is lower alkyl or cycloalkyl X is 0 S or and is phenylalkyl or phenyl optionally substituted by one or more lower alkyl or The pesticidal preparation according to the invention may contain one or more of the following a a an dispersing a an adhesive as well as other known The active substances defined by formula I possess various interesting biocidal They not only act herbicides and but at lower at which no phytotoxic side effects they show a strong lethal action on various representatives of the order acarina mite3 and the insects and soil their eggs and storage for snails and their and bacteria and and worms and The symbol in the general formula I does not include perhalogenated aliphatic residues such as l or Where is a cycloalkyl residue it may Examples of active compounds to be used in the compositions according to the invention are compounds of formula which have an especially good herbicidal In this formula and have the same meaning as with and preferably representing lower or and representing lower alkyl or represents hydrogen or lower alkyl and represents lower alkyl or optionally substituted by alkyl or as exemplified in the following The for of formula are especially distinguished by their fungicidal and ovicidal In this formula and hive the same meaning as in formula with and preferably the meanings given for formula and wherein represents a lower lower alkylphenyl or benzyl as in the following table The active substances of formula I represent benzimidazolylurethanes and Some of them are those of the formula wherein and are independently of each other lower alkyl 1 4 02 or is lower alkyl 1 4 or cycloalkyl 3 6 is lower alkyl 1 phenyl that is unsubstituted or substituted 1 to 3 times by lower alkyl 1 4 or X is sulfur the or alkyl 1 4 0 except that when is methyl and X is cannot One group of compounds of formula are those of the formula wherein the significance given represents hydrogen or lower alkyl and represents lower alkylphenyl or except that when is methyl and is cannot be Another group of compounds of formula are those of the formula wherein and have the significance given and represents a lower lower alk lphenyl or benzyl The new compounds of formula may be manufactured by reacting a benzimidazolyl derivative of formula with a compound of formula B V are wherein A and which are able to form the grouping X II 0 whilst undergoing elimination or the procedure followed will he to in optional a reactive derivative of carbonic acid or acid with imidazole of formula IV and an of formula V an alcohol i i or phe o1 the procedure followed for the formation of the ureas will be to react an imidazole of formula IV with an isocyanate or a carbamic acid whilst in manufacture of urethanes an imidazole of formula IV is reacted with the desired chlorocarbonate The new preparations can be applied in many different for in the form of dusting powders and They can also be worked directly into the j optionally together with Possible materials the manufacture of directly solutions of the compounds of general formula I for j mineral oil fractions of high to medium boiling j for oil coal tar oil and oils of vegetable or animal as well as for 1 alkylated using and furthermore chlorinated for tric ethane and trichlorethylene or benzenes and tetrachlorobenzenes It is advantageous to use i organic solvents having boiling points above j It is especially appropriate to prepare aqueous forms application from emulsion pastes or wettable spraying powders by adding Possible emulsifiers o dispersing agents are products for j sation products of aliphatic amines or carboxylic 13 a Some known benzimidazole compounds have a carbonyl substituent in the similarly as have the compounds of formula I have been exhaustively investigated from the point of view of their chemistry or their possible pharmacological see the articles referred to in CA 8365 The French Patent 1379 540 discloses acid as polymerisation activator for the US Patent describes among other materials acid as sizing agent for paper and Finally benzimidazoles having in a perhalogenated substituent and in either hydrogen or a carbonyl or thiocarbonyl ester are disclosed as herbicidal agents in the French Patent 1 459 782 or the Dutch Patent Applications 66 and 66 The invention is illustrated by the following Examples to which it is not A mixture of g 210 of g of 0 and 70 ml of water is added into a sulfonation The flask is then externally cooled and to the stirred content is at a temperature range of 10 g of Methylthioformate The reaction is slightl When all the methylthioformate is stirring is for 1 The organic layer is then separated from the reaction mixture and dried over Then the solvent distilled off and a oil remains which becomes to Analysis N compound 15 The compounds were also analogous mann point 3 17 Example 2 A etting is manufactured from in the following 20 g of active substance are very finely ground in a pin mill together with 8 g of fine precipitated silicon available under the name as s with 6 g of Bolus g of a condensation product of 1 of octylphenol with about 8 of ethylene oxide and g of sodium thus obtained can be worked up water in any desired to give stable Example 3 was applied in the process to the test plants below using an amount 2 kg of active The application took place 12 days after sowing the test when had developed 1 to 2 Digitaria Beta Chrysanthemum 9 Brassica 9 Amaranthus Soya 2 Cotton 2 V 1 plant plant no longer viable 9 plant Example 4 The urethanes listed in Example showed a good action against weeds in the and in the The following results were achieved fo compounds 23 25 and 1 no damage plant no longer viable 9 plant completely Example 5 Compound was tested for its action mildew Courgette plants Pepo were grown in a green house and sprayed once prophylactically with an aqueous broth of the compound containing increasing quantities of active Two days after the the plants were infected with spores of cichoracearum and after days the plants ere rated as regards fungal a lower inhibitory concentration of 30 ppm of 19 insufficientOCRQuality
Claims (15)
1. Pesticidal preparations containing as an active ingredient a "benzimidazole compound of the general formula wherein ^, 2 and R^ are the same or different and are each hydrogen, halogen, alkyl, -NC^ or CF^, R^ is hydrogen lower alkyl "or cycloalkyl, X is 0, S, -WH- or N-alkyl and Rc is alkyl phehylalkyl or phenyl optionally substituted by one or more halogen, nitro, lower alkyl or CP^ groups.
2. Preparations as claimed in Claim 1, wherein there is present one or more of the following additives: a solvent, a diluent, an emulsifier, a dispersing agent, a thickener, an adhesive as well as other known pesticides.
3. ~ preparations as claimed in Claim 1 or 2, especially a herbicidal preparation, wherein the active component is a compound of formula wherein ^, 2 and ^ have the significance given in Claim 1, Rg represents hydrogen or lower alkyl and R^ represents lower alkyl, phenyl, alk lphenyl or trifluoromethylphenyl. ;> - 20 - 30933/2
4. Preparations as aclaimed in Claim 1 or 2, especially herbicidal, fungicidal or ovicidal preparations, wherein' the active component is a compound of formula wherein R^, R2 and ^ have the significance given in Claim 1, and Rg represents a lower alkyl, phenyl, halophenyl, nitro-phenyl, lower alkylphenyl or benzyl residue.
5. Preparations aa claimed in any one of Claims 1, 2 or 4 especially ovicidal preparations wherein the active component is a compound of formula wherein ^ and R^ have the significance given in Claim 1.
6. Preparations as claimed in any one of Claims 1, 2 or 4» especially herbicidal and fungicidal preparations, wherein the active component is a. compound of formula wherein RQ. represents a lower alkyl, phenyl, halophenyl, nitrophenyl, lower alkylphenyl or benzyl residue. 21 - 30935/2
7. reparations as claimed in any one of Claims 1, 2 or 4, especially herbicidal and fungicidal preparations wherein the active component is a compound of formula wherein and Eg have the significance given in Claim 1.
8. A preparation as claimed in any one of Claims 1, 2 or 4, especially a herbicidal preparation, wherein the active component is the compound of formula
9. A preparation as' claimed in any one of Claims 1, 2 or 4, especially a herbicidal preparation, wherein the active component is the compound of formula
10. , Pesticidal preparations as claimed in Claim 1 and substantially as described in any one of Examples 2 - 5 herein.
11. A method of treating living plants to combat pests, formula I in Claim 1 alone or in the form of a preparation, as claimed in Claim 1.
12. , Benzimidazole compounds of the general formula wherein and R'2 are independently of each other hydrogen, lower alkyl 1- 4 0, CF^, N02 or chlorine, '^ is lower alkyl 1 - 4 C, or cycloalkyl 3- 6 C, R1,. is lower alkyl 1 - 4 C, phenyl that is unsubstituted or substituted 1 to 3 times by halogen, nitro, lower alkyl 1-- 4 0 or OP^, X is oxygen, sulfur the -NH- or -N-lower alkyl 1 - 4 C group, except that when '^ is methyl and X is -NH, R'^ cannot be phenyl.
13. · Benzimidazole compounds according to Claim 12 of the general formula wherein R'^, R'2 and R'^ have the significance given in Claim 12, 'g represents hydrogen or lower alkyl and R* represents lower alkyl, phenyl,, alkylphenyl or trifluoro-methylphenyl, except that when R'^ is methyl and R'g is hydrogen, R'y cannot be phenyl.
14. Benzimidazole compounds according to Claim 12 of the general formula wherein R^, R'2 and R'^ have the significance given in Claim ¾ and R'g represents a lower alkyl, phenyl, halophenyl, nitro-phenyl,- lower alkylphenyl or benzyl residue.
15. Benzimidazole compounds according to Claim 12 sub-, stantially as described in Example 1 herein. PC/rb
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1500567A CH490010A (en) | 1967-10-26 | 1967-10-26 | Pesticides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL30933A0 IL30933A0 (en) | 1968-12-26 |
| IL30933A true IL30933A (en) | 1972-09-28 |
Family
ID=4405528
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL30933A IL30933A (en) | 1967-10-26 | 1968-10-22 | Pesticidal preparations containing benzimidazole compounds and new benzimidazole compounds |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS4936716B1 (en) |
| IL (1) | IL30933A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5475522U (en) * | 1977-11-08 | 1979-05-29 |
-
1968
- 1968-10-22 IL IL30933A patent/IL30933A/en unknown
-
1971
- 1971-08-20 JP JP6305871A patent/JPS4936716B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4936716B1 (en) | 1974-10-02 |
| IL30933A0 (en) | 1968-12-26 |
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