IL30561A - Sulphonic acid salts of substituted guanidines - Google Patents
Sulphonic acid salts of substituted guanidinesInfo
- Publication number
- IL30561A IL30561A IL6830561A IL3056168A IL30561A IL 30561 A IL30561 A IL 30561A IL 6830561 A IL6830561 A IL 6830561A IL 3056168 A IL3056168 A IL 3056168A IL 30561 A IL30561 A IL 30561A
- Authority
- IL
- Israel
- Prior art keywords
- plants
- fungi
- compound
- acid salts
- active
- Prior art date
Links
- 150000002357 guanidines Chemical class 0.000 title description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 23
- 241000233866 Fungi Species 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 10
- 206010039509 Scab Diseases 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 230000003032 phytopathogenic effect Effects 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 14
- 239000002904 solvent Substances 0.000 description 9
- 241000220225 Malus Species 0.000 description 7
- -1 sulphonio Chemical group 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 206010061217 Infestation Diseases 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 241000223600 Alternaria Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- VXLCNTLWWUDBSO-UHFFFAOYSA-N Ethiazide Chemical compound ClC1=C(S(N)(=O)=O)C=C2S(=O)(=O)NC(CC)NC2=C1 VXLCNTLWWUDBSO-UHFFFAOYSA-N 0.000 description 1
- 241000489964 Fusicladium Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000233614 Phytophthora Species 0.000 description 1
- 235000014443 Pyrus communis Nutrition 0.000 description 1
- 241001275899 Salta Species 0.000 description 1
- 241001533598 Septoria Species 0.000 description 1
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XOFFTZJPIPKTBC-UHFFFAOYSA-N methyl n,n-dimethylsulfamate Chemical class COS(=O)(=O)N(C)C XOFFTZJPIPKTBC-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Sulphonic acid salta of substituted guanidines FARBBNFABRIKEN BAYER AKTIENGESBLLSCHAFT C. 28801 of formula (1) in which a sulphonio acid S-alkyllsothiouronium othyl ootoro, 4 toluonooulphonio aoid mothyl or ot&y-l—es-te-re-? 3-iiiti-ob.onBonoouiphonio aoid methyl or otJfry.l o e eaiTCi or dimethyl-aminosulphonic acid methyl esters.
The reaction according to the invention is expediently 'carried out in the presence of a solvent (this term includes mere diluents) . Examples include water and mixtures of water and lower alcohols, such as methanol and ethanol, as well as ethers, such as dioxan or water-immiscible solvents such as hydrocarbons, for example toluene, and chlorinated hydrocarbons, such as chlorobenzene.
The reaction, temperatures can be varied within a fairly wide range. In general, the reaction is carried out at 10 to 120°C, preferably 30 to 100°C.
In carrying out the process according to the invention, approximately 1 mole of the amine of Formula (3) i-s generally used for each mole of the isothiouronium salt of liormula (2). Working up may take place in manner known per se, i'or example by distilling off the solvent in a vacuum.
The active compounds according to the invention exhibit strong fungicidal activity. Because of their low toxicity to warm-blooded animals they are suitable for the control of undesired plant growth and their good compatibility wit higher plants permits their use as plant protection agents against fungal plant diseases.
They are particularly well suited for the control of parasitic fungi on above-soil parts of plants. These fungi include Phytophthora species, Alternaria species, Botrytis cinerea and Septoria species. The active compounds are particularly effective against the causative organisms of scab diseases, such, as apple scab and pear scab, that is the Venturia species .
The active compounds according to the present invention may be produced in known manner, for example by mixing the · active compounds with extenders, that is, liquid or solid diluents or carriers, optionally with the use of surface-active .agents, that .is, * emulsifying agents and/or dispersing agents. In the case of the use of water as an extender, organic, solvents can, for example, also be used as auxiliary solvents.
As liquid diluents or carriers, there are preferably used aromatic hydrocarbons such as xylenes or benzene, chlorinated aromatic hydrocarbons, such as chlorobenzenes, paraffins, such as mineral oil fractions, alcohols, such as methanol- or butanol, or strongly polar solvents, such as dimethyl formamide or dimethyl sulphoxide, as well as water.
As solid diluents or carriers, there are preierably sed. ground natural minerals, such as Kaolins, clays, t>..lc or cnalk, or ground synthetic minerals, such as highly-dispersed silicic acid or silicates. 1 Preferred examples of emulsifying agents include non-ionic, and anionic emulsifiers, such as polyoxyethy!ehe-fatty acid estas-, polyoxyethylene-fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkyl sulphonates and aryl sulphon- ates; and preferred examples of dispersing agents include lignin. sulphite waste liquors and methyl cellulose.
The active compounds may be used as such or in the form of their formulatioris or of the application forms prepared therefrom, ;such as ready-to-use solutions, emulsions, · suspensions, powders, pastes and granulates. Application may take place in the usual manner, for example by spraying,- squirting, watering or scattering.
The concentrations of the active compounds in the ready-to-use application forms can be varied within a wide range. In general, they are from 0.001 to 1#, preferably from 0.003 to 0.5?°. containing as active ingredient a. compound according to the invention in admixture with a solid diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent.
The invention also provides a method of combating fungi which comprises- applying to the fungi or a fungus habitat a compound according to the invention alone or in the form of a composition containing as active ingredient a compound according to the invention in admixture with a solid or. liquid diluent or carrier...
The invention: also provides plants, especially fruit plants., protected from damage by fungi by the application there to of a compound. according to the invention alone or in admixture with a solid or liquid diluent or carrier. The invention also provides fruit grown on such plants.
The fungicidal effectiveness of the compounds of the invention is illustrated- by the - following Examples A-C.
Example A Fusicladium test (apple scab) (Protective) Solvent: 4.7- parts by weight acetone Emulsifier: 0.3 part by weight alkylaryl polyglycol ether Water:. 95 parts by weight The amount of active compound required for the desired concentration of the active compound in the spray liquid is mixed with the stated amount of solvent, and the concentrate is diluted with the stated amount of water which contains the stated additions.
Young apple seedlings in the 4-6 leaf stage are sprayed with the spray liquid. until dripping wet. The plants remain in a greenhouse for 24 hours at 20°C and at a relative atmospheric humidity of 70#. They are then inoculated with an aqueous. conidium suspension of the apple scab causative organ humidity of 100#.
The plants then again come into a greenhouse for 14 days. days after inoculation, the infestation of the seedlings is determined as a percentage of the untreated but also inoculated control plants.
Qo means no infestation; 100$ means that the infestation is exactly as great as in the case of the control plants.
The active compounds, the concentrations of the active compounds and the results can be seen from the following Table 1: 30561/2 Table 2 (Contd) Pusicladjum test (Protective) Infestation as a percentage of the. infestation of the untreated control with a concentration of active compound (in ) of Active compound 0.0062 Pusicladium test (apple scab) [Curative] Solvent: 4.7 parts b weight acetone Emulsifier: 0.3 part by weight alkylaryl polyglycol ether Water: 95 parts by weight The amount of active compound required for the desired concentration of the active compound in the spray liquid is mixed with the stated amount of solvent, and the concentrate is diluted with the stated . amount of water which contains the stated additions.
Young apple seedlings in the 4 - 6 leaf stage are inoculated with an aqueous - conidium suspension of the apple scab causative organism Pusicladium dendriticum Puck and incubated for 18 hours in a humidity chamber at 18-20°C and at an atmospheric humidity of 100$. The plants then come into a greenhouse. They dry.
After standing for a suitable period of time, the plants are sprayed dripping wet with the spray liquid prepared in the manner described above. The plants then again oome into Le A 11004 - 10 - The process of the invention is illustrated by the following Example 1;- Example 1 .
Claims (1)
1. 30561/2 according to any of Claims 1 to 9 Or 15 In dmixture with a solid diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent. 17. A composition according to Claim 16 containing from 0.001 to 95$ and preferably from 0.001 to 1% by weight of the active compound. ;; 18. A method of combating phytopathogenic fungi which oomprlses applying t-o such fungi or fungus habitat a compound according to any of Claims 1 to 9 or 15 alone or in tie form of a composition according to Claims 16 or 17. 19. A method according to Claim 18 in which a composition is used containin from 0.001 to 1$ by weight of the active compound. 20. A method according to Claim 18 or 19 in which the fungi are the causative organisms of scab diseases of plants* 21. method accordin to any of Claims 18 to 20 in which the compound is one of those hereinbefore mentioned in Example A.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0053606 | 1967-09-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL30561A0 IL30561A0 (en) | 1968-10-24 |
| IL30561A true IL30561A (en) | 1971-12-29 |
Family
ID=7106465
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL6830561A IL30561A (en) | 1967-09-15 | 1968-08-16 | Sulphonic acid salts of substituted guanidines |
Country Status (2)
| Country | Link |
|---|---|
| IL (1) | IL30561A (en) |
| NL (1) | NL6813057A (en) |
-
1968
- 1968-08-16 IL IL6830561A patent/IL30561A/en unknown
- 1968-09-12 NL NL6813057A patent/NL6813057A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL30561A0 (en) | 1968-10-24 |
| NL6813057A (en) | 1969-03-18 |
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