GB2162423A - Oil-in-water dispersion of a sulfenyl carbamate for agricultural use - Google Patents
Oil-in-water dispersion of a sulfenyl carbamate for agricultural use Download PDFInfo
- Publication number
- GB2162423A GB2162423A GB08519067A GB8519067A GB2162423A GB 2162423 A GB2162423 A GB 2162423A GB 08519067 A GB08519067 A GB 08519067A GB 8519067 A GB8519067 A GB 8519067A GB 2162423 A GB2162423 A GB 2162423A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dispersion
- weight
- water
- compound
- polyvinyl alcohol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000006185 dispersion Substances 0.000 title claims abstract description 44
- -1 sulfenyl carbamate Chemical compound 0.000 title claims abstract description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 239000004372 Polyvinyl alcohol Substances 0.000 claims abstract description 30
- 229920002451 polyvinyl alcohol Polymers 0.000 claims abstract description 30
- 239000004202 carbamide Substances 0.000 claims abstract description 27
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 238000007127 saponification reaction Methods 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 230000000749 insecticidal effect Effects 0.000 abstract description 17
- 239000000203 mixture Substances 0.000 description 22
- 239000002245 particle Substances 0.000 description 14
- 238000010790 dilution Methods 0.000 description 13
- 239000012895 dilution Substances 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 9
- 229940125904 compound 1 Drugs 0.000 description 9
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 239000004495 emulsifiable concentrate Substances 0.000 description 6
- 238000001000 micrograph Methods 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 239000004593 Epoxy Chemical class 0.000 description 5
- 229940126214 compound 3 Drugs 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000002562 thickening agent Substances 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 229940125898 compound 5 Drugs 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 235000012424 soybean oil Nutrition 0.000 description 3
- 239000003549 soybean oil Substances 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 2
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 230000007794 irritation Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- JVKRKMWZYMKVTQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JVKRKMWZYMKVTQ-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 244000144730 Amygdalus persica Species 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- 229920002907 Guar gum Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 229920000161 Locust bean gum Polymers 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000012897 dilution medium Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 235000010420 locust bean gum Nutrition 0.000 description 1
- 239000000711 locust bean gum Substances 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
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/22—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients stabilising the active ingredients
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
An oil-in-water dispersion for agricultural use which is excellent in dispersibility and stability of the insecticidal component during storage comprises 1 to 70% by weight of a sulfenyl carbamate derivative, 1 to 20% by weight of polyvinyl alcohol, 0.5 to 10% by weight of a urea compound and the remainder of water.
Description
SPECIFICATION
Oil-in-water dispersion for agricultural use
The present invention relates to an oil-in-water dispersion for agricultural use and more particularly to a dispersion comprising a sulfenyl carbamate derivative as an insecticidal component, the derivative being represented by the general formula
wherein Ar is
R1 and R2 are same or different and are each C18 alkyl, C36 cycloalkyl, phenyl, substituted phenyl, benzyl, -X-COOR3 or -Y-CN, X and Y being each C16 alkylene and R3 being C18 alkyl or C36 cycloalkyl; or R1 is C18 alkyl,
R2 is
R4 being C18 alkyl.
Conventionally, a pesticide in the form of an emulsifiable concentrate or wettable powder is known as a pesticide which can be applied in a liquid form. The emulsifiable concentrate is prepared by dissolving an insecticidal component and a surfactant in an organic solvent. The emulsifiabie concentrate has a problem in toxicity and irritation to mammalia and in causing phytotoxicity against crops, due to the presence of the surfactant and the organic solvent.
Further, the organic solvent entails bad smell and danger to catch fire, and accompanies difficulty in handling the emulsifiable concentrate. On the other hand, the wettable powder comprises an insecticidal component, inorganic carrier and a dispersant. Although the powder has no disadvantage derived from the organic solvent, the power is apt to be scattered in the preparation of the aqueous solution and is difficult to be handled. Further, the resulting aqueous solution is poor in stability and the inorganic carrier is subject to sedimentation. Thus, the wettable powder has a problem that it is hardly sprayable in ultra-low-volume (ULV) in the aerial application.
In recent years, various dispersions are proposed which comprise water and a hydrophobic insecticidal component dispersed therein in the form of fine particles in Japanese Unexamined
Patent Publication (Kokai Koho) Nos. 17,301/1980, 124,707/1980, 49,303/1981, 49,307/1981, 120,608/1981, 192,810/1983, 118,501/1983, etc. These dispersions contain as an active ingredient organophosphorous insecticide or synthetic pyrethroid, in addition to polyvinyl alcohol, thickening agent and other additives.
On the other hand, the sulfenyl carbamate derivative of the general formula [I] is disclosed in
Japanese Kokai Koho Nos. 48,137/1975, 200,377/1982, 92,655/1983, 11,863/1978, etc. and is known as a useful insecticide having high insecticidal activity and low toxicity to warm-blooded animals. Thus, if the sulfenyl carbamate derivative of the general formula [l can be dispered in water to prepare an oil-in-water dispersion, it will eliminate defects of the above conventional pesticides, will be spread in a small amount at a high concentration and will have an advantage as a safty seed-treating agent. However, the sulfenyl carbamate derivative [I] has been known to be poor in storage stability, particularly in water.Conventionally, tertiary amines, epoxy compounds, etc. are added to the emulsifiable concentrate, aqueous solution etc. of the derivative [I], in order to improve the stability thereof. Oil-in-water dispersion with addition of tertiary amines, however, loses its dispersibility due to gelation during a long period of storage.
Further, in oil-in-water dipersion prepared with addition of epoxy compound or with no stabilizer, the insecticidal component decomposes in about 10 to 30%, hence unsatisfactory. In these cases, the desired dispersion can not be obtained.
An object of the invention is to provide an oil-in-water dispersion which is excellent in dispersibility and stability of the insecticidal component during storage.
The above and other objects of the invention will be apparent from the following description.
The present invention provides an oil-in-water dispersion for agricultural use comprising 1 to 70% by weight of the sulfenyl carbamate derivative represented by the above general formula [I], 1 to 20% by weight of polyvinyl alcohol, 0.5 to 10% by weight of a urea compound and the remainder of water.
In the general formula [I], examples of useful C18 alkyl groups are methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, etc. Examples of useful C3a cycloalkyl groups are cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Examples of substituted phenyl groups are chlorophenyl, methylphenyl, methoxyphenyl, etc. Examples of useful C18 alkylene groups are methylene, ethylene, propylene, hexylene, etc.
The followings are typical examples of the sulfenyl carbamate derivatives useful in the invention.
2, 3-dihydro-2, 2-dimethylbenzofuran-7-yl N-(N-ethoxycarbonylethyl-N-isopropylaminosulfenyl)
N-methyl carbamate (Compound 1) o 2,3-dihydro-2,2-dimethylbenzofuran-7-yl N-[N , N-bis(ethoxycarbonyl methyl)aminosulfenyl] Nmethyl carbamate (Compound 2) 2, 3-dihydro-2,2-dimethylbenzofuran-7-yl N-(N , N-dibutylaminosu Ifenyl) N-methyl carbamate (Compound 3) S-methyl N[[N-methyl(N-isobutyl-N-ethoxycarbonylethylaminothio)carbamoyl]oxyjthioacetoimi- date (Compound 4) S-methyl N [[N-methyl(N-benzyl-N-ethoxycarbonylethylami nothio)carbamoyl]oxy]thioacetoi mi- date (Compound 5) O-butyl 0'-(2, 3-dihydro-2, Zdimethylbenzof uran--/-yl) N, N '-dimethyl N, N'-thiodicarbamate (Compound 6)
The sulfenyl carbamate derivative is contained in the present dispersion usually in an amount of 1 to 70 % by weight, preferably 10 to 60% by weight. With less than 1 % by weight of the sulfenyl carbamate derivative, a lot of polyvinyl alcohol is required to maintain the dispersion stable, hence unpractical. With more than 70% by weight of the derivative, the dispersion become high in viscosity and difficult to use, hence also unpractical.
Polyvinyl alcohol used in the invention is not limited particularly in saponification degree or polymerization degree, but preferably has saponification degree of 70 to 90 mole% and polymerization degree of 200 to 3500. Typical examples thereof are polyvinyl alcohol 205 product of Kuraray Co., Ltd., saponification degree 87 to 89 mole%, polymerization degree 500 to 600], polyvinyl alcohol 224 [product of Kuraray Co., Ltd., saponification degree 87 to 89 mole%, polymerization degree 2400 to 2500], etc. The proportion of polyvinyl alcohol varies depending on the amount and kind of the sulfenyl carbamate derivative, but is usually 1 to 20% by weight, preferably 1.5 to 12% by weight. With less than 1 % by weight of polyvinyl alcohol, the dispersion become poor in stability and hardly stored for a long period of time.With more than 20% by weight, the dispersion is high in viscosity, hence unpractical.
In the invention, it is essential to add a urea compound to maintain stability of the insecticidal component. Examples of useful urea compounds are urea, methylurea and like lower alkyl urea, etc. The urea compound is used in 0.5 to 10% by weight, preferably 1 to 5% by weight. When the urea compound is used less than 0.5% by weight, the insecticidal component is poor in stability during storage. It is uneconomical to use more than 10% by weight because the stability is same.
In the invention, it is possible to add an epoxy compound to further enhance the stability of the insecticidal component. Examples of useful epoxy compounds are epoxidized soybean oil, phenyl glycidyl ether, glycidol, etc. The epoxy compound can be used in an amount of 0.5 to 10% by weight, preferably 1 to 5% by weight of the insecticidal component.
To the present dispersion, when desired, may be added a thickening agent, surfactant, etc.
Examples of useful thickening agents are sodium polyacrylate, ammonium polyacrylate, sodium salt of carboxymethyl cellulose, hydroxyethyl cellulose, methyl cellulose, polyethylene glycol, gelatin, starch, casein, sodium alginate, guar gum, locust bean gum, xanthan gum, etc.
Examples of useful surfactants are alkylsulfate ester, alkylbenzenesulfonic acid salt, dialkylsulfosuccinic acid salt, polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, sorbitan fatty acid ester, polyoxyethylene fatty acid ester, oxyethylene oxypropylene block polymer, polyoxyethylene alkylamine, alkylbetaine, etc. These thickening agent or surfactant can be used usually up to 5% by weight in the present dispersion.
The present composition can be prepared by dispersing the liquid sulfenyl carbamate derivative in an aqueous mixture of polyvinyl alcohol and the urea compound by mechanical means. For example, the dispersion is prepared by dispersing the liquid sulfenyl carbamate derivative which is heated when desired, in an aqueous solution of polyvinyl alcohol and the urea compound at a temperature of from room temperature to 70"C with use of an ultra high speed homogenizer such as Polytron, a product of Kinematica GmbH, Switzerland. The mixture is stirred preferably for 5 to 10 minutes. The stirring is continued until the particles become 1 to 5 y in mean size and all of them become up to 1 OIL, preferably up to 5IL in size. A surfactant may be added and a thickening agent can also be added at a final stage.
The present composition can be used without dilution, or used after diluted in a wide range, e.g., at low dilution ratio such as several to several tens times or at high dilution ratio such as 1000 to 2000 times. A carrier or water is used as a dilution medium to prepare the dispersion having the desired concentration. The present composition is used as a foliar spray, soil-treating agent, seed-treating agent with or without dilution.
The present composition is excellent in dispersibility and stability of the insecticidal component for a long period of time. Further, the composition has an excellent biological activity comparable to the conventional liquid type formulations and has advantages which do not exist in the case of the conventional formulations. Namely, the present composition can be made into from a low concentration to a high concentration of 70% by weight, entails no damage to crops because of using no organic solvent, has little irritation to eyes or skin, is incombustible and causes almost no stain or damage on articles. Further, the present composition can be diluted with inorganic salt-containing water at a high concentration, which is hardly used in conventional emulsifiable concentrate.
The present invention will be described in more detail with reference to examples, test examples and reference examples.
Example 1
A 22.2g-quantity of Compound 1 (content of active ingredient: 90%), 3g of urea, 50g of 10% by weight aqueous solution of Polyvinyl alcohol 224 and 24.89 of water were admixed at room temperature by use of Polytron at 10000rpm for 5 minutes. All of particles were up to 1011 in size and 3IL in mean particle size by microphotograph. The obtained dispersion was excellent in dilution with water. The dispersion was placed into a tightly-sealed container at 50"C for 30 days and exhibited an excellent stability without causing separation of an oil layer.
Example 2
A 66.6g-quantity of Compound 1 (content of active ingredient: 90%), 39 of urea, 209 of 10% by weight aqueous solution of Polyvinyl alcohol 205 and 10.49 of water were admixed at room temperature by use of Polytron at 10000rpm for 5 minutes. All of particles were up to 1 orb in size and 2IL in mean particle size by microphotograph. The obtained dispersion was excellent in dilution with water. The dispersion was placed into a tightly-sealed container at 50"C for 30 days and exhibited an excellent stability without causing separation of an oil layer.
Example 3
A 42.4g-quantity of Compound 5 (content of active ingredient: 94%), 2g of urea, 309 of 10% by weight aqueous solution of Polyvinyl alcohol 224 and 25.69 of water were admixed at 50"C by use of Polytron at 10000rpm for 5 minutes. All of particles were up to 10y in size and 3IL in mean particle size by microphotograph. The obtained dispersion was excellent in dilution with water. The dispersion was placed into a tightly-sealed container at 50"C for 30 days and exhibited an excellent stability without causing separation of an oil layer.
Examples 4 to 12
Dispersions of Examples 4 to 1 2 were prepared in the same manner as in Examples 1 to 3.
Table I showed the proportions of ingredients of composition and its stability. In Examples 5 and 11, epoxidized soybean oil was added in an amount of 2% by weight of the active ingredient.
Table II
Composition Decompn. rate after 30 days (%) 40 C | 50 C Example 1 0. 25 1. 24 2 0. 31 2. 20 3 0. 11 1. 1 5 4 0. 21 1. 14 5 0. 04 0. 55 6 0. 20 1. 05 7 0. 45 1. 84 8 0. 30 2. 09 9 0. 25 1. 10 10 0. 16 1. 1 8 1 1 0. 1 6 0. 98 12 0. 13 1. 3 1 13 0. 11 1. 14 Ref. Ex. 1 8. 2 5 2 3. 6 0 2 5. 94 18. 21 3 gellation In the stability at 50"C for 30 days, "good" means no oil layer separated when the dispersion was placed into a tightly-sealed container at 50'C for 30 days. In the dilution test with water, "good" is given in case the composition was homogeneously dispersed within 30 seconds when the composition was added to water in such amount that the dilution ratio was 100 to 1000 times and stirred with a magnetic stirrer.
Reference Example 1
A 22.2g-quantity of Compound 1 (content of active ingredient: 90%), 509 of 10% by weight aqueous solution of Polyvinyl alcohol 224 and 27.8g of water were admixed at room temperature by use of Polytron at 10000rpm for 5 minutes. All of particles were up to 10IL in size and 3,u in mean particle size by micro-photograph. The obtained dispersion was excellent in dilution with water. The dispersion was placed into a tightly-sealed container at 50"C for 30 days. No separation of an oil layer occurred.
Reference Example 2
A 56.8g-quantity of Compound 3 (content of active ingredient: 88%), 30g of 10% by weight aqueous solution of Polyvinyl alcohol 205, 5 g of epoxidized soybean oil and 8.2g of water were admixed at room temperature by use of Polytron at 10000rpm for 5 minutes. All of particles were up to 1 0it in size and 2y in mean particle size by microphotograph. The obtained dispersion was excellent in dilution with water. The dispersion was placed into a tightly-sealed container at 50"C for 30 days. No separation of an oil layer occurred.
Reference Example 3
A 44.4g-quantity of Compound 1 (content of active ingredient: 90%), 25g of 20% by weight aqueous solution of Polyvinyl alcohol 205, 8 g of triethanolamine and 22.69 of water were admixed at room temperature by use of Polytron at 10000rpm for 5 minutes. All of particles were up to 101l in size and 3,u in mean particle size by microphotograph. The obtained dispersion was excellent in dilution with water. The dispersion was placed into a tightly-sealed container at 50"C for 30 days. The dispersion gelled and was not usable.
Test Example 1
Compositions of the above Examples and Reference Examples were tested for storage stability of the insecticidal component. The composition was placed into a tightly-sealed container at 40"C or 50"C for 30 days and then concentration of the insecticidal component was measured to calculate decomposition rate. Table II showed decomposition rate of each composition.
T a b l e I
Active ingredient Urea compd. Polyvinyl alcohol Mean Stability Dilution Ex. particle at 50 C with (content: %) (content: %) (content: %) size ( ) for 30 days water 4 Compound 1 Urea Polyvinyl alcohol 3 good good (40) (3) 205 (5) 5 Compound 1 Urea Polyvinyl alcohol 3 good good (40) (3) 205 (5) 6 Compound 1 Urea Polyvinyl alcohol 4 good good (40) (8) 205 (5) 7 Compound 2 Urea Polyvinyl alcohol 2 good good (30) (3) 205 (7) 8 Compound 3 Urea Polyvinyl alcohol 3 good good (20) (3) 205 (10) 9 Compound 3 Urea Polyvinyl alcohol 2 good good (50) (3) 205 (2) 10 Compound 4 Urea Polyvinyl alcohol 3 good good (40) (3) 205 (2) 11 Compound 4 Urea Polyvinyl alcohol 2 good good (30) (3) 205 (6) 12 Compound 5 Urea Polyvinyl alcohol 3 good good (20) (3) 205 (12) 13 Compound 6 Urea Polyvinyl alcohol 2 good good (20) (3) 205 (10) As shown in Table II, compositions of Examples 1 to 12 having added urea derivative therein were excellent in stability of the insecticidal component, but those of Reference Examples 1 and 2 were unstable and could not be used practically.
Test Example 2
Compositions of Examples were tested for biological activity in comparison with conventional pesticide composition in spray test. Table Ill gave comparison of the insecticidal activity. In the
Table, the emulsifiable concentrates (E.C.) are prepared by the conventional formulations.
T a b l e III
Active Mortality Mortality E x a m p I e ingredient of green peach of tabacco (ppm) aphid (%) outworn (%) Example 1 2 0 0 1 0 0 6 0 Compound 1 (20% E.C.) 200 95 45 Example 8 2 0 0 9 5 5 0 Compound 3 (20% E.C.) 200 60 20 Example 11 4 0 0 4 5 1 0 0 Compound 4 (30% E.C.) 400 30 90 Example 1 2 4 0 0 6 0 1 0 0 Compound 5 (20% E.C.) 400 50 8 5 Example 1 3 2 0 0 1 0 0 5 0 Compound 6 (20% E.C.) 200 90 40
Claims (8)
1. An oil-in-water dispersion for agricultural use comprising 1 to 70% by weight of sulfenyl carbamate derivative, 1 to 20% by weight of polyvinyl alcohol, 0.5 to 10% by weight of a urea compound and the remainder of water, the sulfenyl carbamate derivative being represented by the general formula
wherein Ar is
R, and R2 are same or different and are each C18 alkyl, C36 cycloalkyl, phenyl, substituted phenyl, benzyl, -X-COOR3 or -Y-CN, X and Y being each C16 alkylene and R3 being C1#8 alkyl or C36 cycloalkyl; or R, is C1#8 alkyl,
R4 being C1'-'8 alkyl.
2. A dispersion is defined in claim 1 wherein Ar is
R1 is -CH2CH2COOC2H5 and R2 is isopropyl.
3. A dispersion as defined in claim 1 wherein Ar is
R1 and R2 are both n-butyl.
4. A dispersion as defined in claim 1 wherein
Ar is
R1 is -CH2CH2COOC2Hs and R2 is benzyl.
5. A dispersion as defined in claim 1 wherein
Ar is
R1 is -CH2CH2COOC2H5 and R2 is isobutyl.
6. A dispersion as defined in claim 1 wherein polyvinyl alcohol has a polymerization degree of 200 to 3500 and a saponification degree of 70 to 90 mole%.
7. A dispersion as defined in claim 1 wherein the urea compound is at least one selected from the group consisting of urea and lower alkyl urea.
8. An oil-in-water dispersion for agricultural use substantially as hereinbefore described with reference to and as illustrated by the examples herein set forth.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16207784A JPS6137707A (en) | 1984-07-31 | 1984-07-31 | Agricultural oil-in-water type dispersible composition |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8519067D0 GB8519067D0 (en) | 1985-09-04 |
| GB2162423A true GB2162423A (en) | 1986-02-05 |
| GB2162423B GB2162423B (en) | 1988-01-13 |
Family
ID=15747643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08519067A Expired GB2162423B (en) | 1984-07-31 | 1985-07-29 | Oil-in-water dispersion of a sulfenyl carbamate for agricultural use |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS6137707A (en) |
| BR (1) | BR8503623A (en) |
| ES (1) | ES8707080A1 (en) |
| FR (1) | FR2568451B1 (en) |
| GB (1) | GB2162423B (en) |
| IT (1) | IT1187720B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0357559A3 (en) * | 1988-09-02 | 1992-01-22 | AgrEvo UK Limited | Aqueous formulations and their use |
| WO2007034275A3 (en) * | 2005-09-19 | 2007-07-05 | Battelle Uk Ltd | Formulations for improved stability of pest control agents |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05339104A (en) * | 1992-06-04 | 1993-12-21 | Sumitomo Chem Co Ltd | Method for preparing wettable powder diluent for seed treatment |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5517301A (en) * | 1978-07-07 | 1980-02-06 | Sumitomo Chem Co Ltd | O/w suspension of pesticidal composition |
| JPS55124707A (en) * | 1979-03-16 | 1980-09-26 | Sumitomo Chem Co Ltd | Oil-in-water-type insecticidal suspension composition |
-
1984
- 1984-07-31 JP JP16207784A patent/JPS6137707A/en active Granted
-
1985
- 1985-07-29 GB GB08519067A patent/GB2162423B/en not_active Expired
- 1985-07-30 BR BR8503623A patent/BR8503623A/en not_active IP Right Cessation
- 1985-07-31 FR FR858511677A patent/FR2568451B1/en not_active Expired
- 1985-07-31 ES ES545779A patent/ES8707080A1/en not_active Expired
- 1985-07-31 IT IT21771/85A patent/IT1187720B/en active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0357559A3 (en) * | 1988-09-02 | 1992-01-22 | AgrEvo UK Limited | Aqueous formulations and their use |
| WO2007034275A3 (en) * | 2005-09-19 | 2007-07-05 | Battelle Uk Ltd | Formulations for improved stability of pest control agents |
Also Published As
| Publication number | Publication date |
|---|---|
| IT8521771A0 (en) | 1985-07-31 |
| ES8707080A1 (en) | 1987-07-16 |
| GB8519067D0 (en) | 1985-09-04 |
| JPH0557964B2 (en) | 1993-08-25 |
| JPS6137707A (en) | 1986-02-22 |
| IT1187720B (en) | 1987-12-23 |
| BR8503623A (en) | 1986-04-29 |
| GB2162423B (en) | 1988-01-13 |
| FR2568451A1 (en) | 1986-02-07 |
| FR2568451B1 (en) | 1989-03-03 |
| ES545779A0 (en) | 1987-07-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19960729 |