CA1305050C - Bis-alkylthioakylamino-n-alkycarbamates thermiquement stables - Google Patents

Bis-alkylthioakylamino-n-alkycarbamates thermiquement stables

Info

Publication number: CA1305050C
Authority: CA; Canada
Prior art keywords: alkali metal; thermal decomposition; composition; mass; alkyl
Prior art date: 1985-04-18
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.): Expired - Lifetime

Application number

CA000506171A

Other languages

English (en)

Inventor

David Lucas Miles

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Rhone Poulenc Nederland BV

Original Assignee

Rhone Poulenc Nederland BV

Priority date (The priority date 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 date listed.)

1985-04-18

Filing date

1986-04-09

Publication date

1992-07-14

1986-04-09 Application filed by Rhone Poulenc Nederland BV filed Critical Rhone Poulenc Nederland BV

1992-07-14 Application granted granted Critical

1992-07-14 Publication of CA1305050C publication Critical patent/CA1305050C/fr

2009-07-14 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

150000004657 carbamic acid derivatives Chemical class 0.000 title 1
239000000575 pesticide Substances 0.000 claims abstract description 35
238000005979 thermal decomposition reaction Methods 0.000 claims abstract description 20
239000004563 wettable powder Substances 0.000 claims abstract 4
239000000203 mixture Substances 0.000 claims description 50
150000001875 compounds Chemical class 0.000 claims description 27
238000000034 method Methods 0.000 claims description 22
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 16
229910052783 alkali metal Inorganic materials 0.000 claims description 13
229910019142 PO4 Inorganic materials 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 12
-1 alkythio Chemical group 0.000 claims description 12
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 12
239000010452 phosphate Substances 0.000 claims description 12
238000002156 mixing Methods 0.000 claims description 9
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
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 claims description 7
239000011734 sodium Substances 0.000 claims description 7
229910052708 sodium Inorganic materials 0.000 claims description 7
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 5
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
230000002401 inhibitory effect Effects 0.000 claims description 5
229910052700 potassium Inorganic materials 0.000 claims description 5
239000011591 potassium Substances 0.000 claims description 5
150000001340 alkali metals Chemical class 0.000 claims description 4
230000000361 pesticidal effect Effects 0.000 claims description 4
230000000979 retarding effect Effects 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
125000001589 carboacyl group Chemical group 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
239000003112 inhibitor Substances 0.000 claims 11
229910000288 alkali metal carbonate Inorganic materials 0.000 claims 3
150000008041 alkali metal carbonates Chemical class 0.000 claims 3
229940005740 hexametaphosphate Drugs 0.000 claims 3
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims 3
BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 claims 3
125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 2
230000000087 stabilizing effect Effects 0.000 claims 2
125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 9
229910052717 sulfur Inorganic materials 0.000 abstract description 9
239000011593 sulfur Substances 0.000 abstract description 9
239000000356 contaminant Substances 0.000 abstract description 6
239000012669 liquid formulation Substances 0.000 abstract description 3
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract description 2
238000000354 decomposition reaction Methods 0.000 description 17
XDOTVMNBCQVZKG-UHFFFAOYSA-N methyl n-[methyl-[methyl-(1-methylsulfanylethylideneamino)oxycarbonylamino]sulfanylcarbamoyl]oxyethanimidothioate Chemical compound CSC(C)=NOC(=O)N(C)SN(C)C(=O)ON=C(C)SC XDOTVMNBCQVZKG-UHFFFAOYSA-N 0.000 description 15
239000007787 solid Substances 0.000 description 15
239000005916 Methomyl Substances 0.000 description 14
238000009472 formulation Methods 0.000 description 13
UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
239000007788 liquid Substances 0.000 description 10
239000002245 particle Substances 0.000 description 9
239000003381 stabilizer Substances 0.000 description 9
239000000843 powder Substances 0.000 description 8
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical class C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 7
239000006185 dispersion Substances 0.000 description 7
239000004615 ingredient Substances 0.000 description 7
239000002270 dispersing agent Substances 0.000 description 6
238000001035 drying Methods 0.000 description 6
150000003839 salts Chemical class 0.000 description 6
239000002253 acid Substances 0.000 description 5
125000004429 atom Chemical group 0.000 description 5
230000000694 effects Effects 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
239000000080 wetting agent Substances 0.000 description 5
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
241000607479 Yersinia pestis Species 0.000 description 4
150000002484 inorganic compounds Chemical class 0.000 description 4
229910010272 inorganic material Inorganic materials 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
239000002002 slurry Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
229910015400 FeC13 Inorganic materials 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
239000000654 additive Substances 0.000 description 3
239000000872 buffer Substances 0.000 description 3
239000000969 carrier Substances 0.000 description 3
125000002091 cationic group Chemical group 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
235000015165 citric acid Nutrition 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
235000019799 monosodium phosphate Nutrition 0.000 description 3
125000004430 oxygen atom Chemical group O* 0.000 description 3
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 3
229910000162 sodium phosphate Inorganic materials 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
YWHLKYXPLRWGSE-UHFFFAOYSA-N Dimethyl trisulfide Chemical compound CSSSC YWHLKYXPLRWGSE-UHFFFAOYSA-N 0.000 description 2
241000238631 Hexapoda Species 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
239000007836 KH2PO4 Substances 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000000996 additive effect Effects 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
230000002939 deleterious effect Effects 0.000 description 2
WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 2
235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
229910001385 heavy metal Inorganic materials 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
230000002209 hydrophobic effect Effects 0.000 description 2
TYEVWCPZVQACAE-ONEGZZNKSA-N methyl (1e)-n-hydroxyethanimidothioate Chemical compound CS\C(C)=N\O TYEVWCPZVQACAE-ONEGZZNKSA-N 0.000 description 2
239000002808 molecular sieve Substances 0.000 description 2
229910000402 monopotassium phosphate Inorganic materials 0.000 description 2
235000019796 monopotassium phosphate Nutrition 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
150000002978 peroxides Chemical class 0.000 description 2
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
238000001694 spray drying Methods 0.000 description 2
230000006641 stabilisation Effects 0.000 description 2
238000011105 stabilization Methods 0.000 description 2
239000008107 starch Substances 0.000 description 2
150000003871 sulfonates Chemical class 0.000 description 2
208000006379 syphilis Diseases 0.000 description 2
238000009736 wetting Methods 0.000 description 2
BYJQAPYDPPKJGH-UHFFFAOYSA-N 3-(2-carboxyethyl)-1h-indole-2-carboxylic acid Chemical compound C1=CC=C2C(CCC(=O)O)=C(C(O)=O)NC2=C1 BYJQAPYDPPKJGH-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241001630921 Chlorida Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical class N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
240000006240 Linum usitatissimum Species 0.000 description 1
231100000674 Phytotoxicity Toxicity 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
IOEJYZSZYUROLN-UHFFFAOYSA-M Sodium diethyldithiocarbamate Chemical compound [Na+].CCN(CC)C([S-])=S IOEJYZSZYUROLN-UHFFFAOYSA-M 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000006177 alkyl benzyl group Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
229910000323 aluminium silicate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000003254 anti-foaming effect Effects 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
239000003139 biocide Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000004927 clay Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
238000005056 compaction Methods 0.000 description 1
108010057108 condensin complexes Proteins 0.000 description 1
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical class Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
238000001514 detection method Methods 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000004205 dimethyl polysiloxane Substances 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
229950004394 ditiocarb Drugs 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000010685 fatty oil Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
239000003906 humectant Substances 0.000 description 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000003999 initiator Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical class Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
239000000944 linseed oil Substances 0.000 description 1
235000021388 linseed oil Nutrition 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
230000002101 lytic effect Effects 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
XDOTVMNBCQVZKG-NTLHZVPKSA-N methyl (1e)-n-[methyl-[methyl-[(z)-1-methylsulfanylethylideneamino]oxycarbonylamino]sulfanylcarbamoyl]oxyethanimidothioate Chemical compound CS\C(C)=N/OC(=O)N(C)SN(C)C(=O)O\N=C(/C)SC XDOTVMNBCQVZKG-NTLHZVPKSA-N 0.000 description 1
CRVVHBFLWWQMPT-UHFFFAOYSA-N naphthalene-1-sulfonic acid;sodium Chemical compound [Na].C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 CRVVHBFLWWQMPT-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
125000004334 oxygen containing inorganic group Chemical group 0.000 description 1
LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
238000005453 pelletization Methods 0.000 description 1
HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
230000002265 prevention Effects 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000000779 smoke Substances 0.000 description 1
APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003464 sulfur compounds Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
239000011800 void material Substances 0.000 description 1
239000010457 zeolite Substances 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
- 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)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000506171A 1985-04-18 1986-04-09 Bis-alkylthioakylamino-n-alkycarbamates thermiquement stables Expired - Lifetime CA1305050C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US72455685A	1985-04-18	1985-04-18
US724,556		1985-04-18

Publications (1)

Publication Number	Publication Date
CA1305050C true CA1305050C (fr)	1992-07-14

Family

ID=24910903

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000506171A Expired - Lifetime CA1305050C (fr)	1985-04-18	1986-04-09	Bis-alkylthioakylamino-n-alkycarbamates thermiquement stables

Country Status (14)

Country	Link
EP (1)	EP0218698A1 (fr)
JP (1)	JPS62502542A (fr)
KR (1)	KR930008436B1 (fr)
AU (1)	AU594053B2 (fr)
BR (1)	BR8606630A (fr)
CA (1)	CA1305050C (fr)
ES (1)	ES8707650A1 (fr)
GR (1)	GR861005B (fr)
IL (1)	IL78508A0 (fr)
MX (1)	MX162186A (fr)
MY (1)	MY101393A (fr)
TR (1)	TR23438A (fr)
WO (1)	WO1986005950A1 (fr)
ZA (1)	ZA862900B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL99078A0 (en) *	1990-08-06	1992-07-15	Du Pont	Bis-(hydroximidoyl chloride)derivatives,fungicidal compositions containing them and their use as fungicides
TW200640368A (en) *	2005-02-14	2006-12-01	Du Pont	Method for controlling insect pests on plants

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK302478A (da) *	1977-09-28	1979-03-29	Du Pont	Insecticid
US4297370A (en) *	1979-11-27	1981-10-27	E. I. Du Pont De Nemours And Company	Insecticidal compositions
BR8104086A (pt) *	1980-07-03	1982-03-16	Du Pont	Processo para o controle de carrapatos
GB2085369A (en) *	1980-07-17	1982-04-28	Turner David Robin	Cargo support means
AR229041A1 (es) *	1981-01-21	1983-05-31	Union Carbide Corp	Concentrado plaguicida acuoso no reopectico de un sulfuro de biscarbamoilo simetrico n-sustituido

1986
- 1986-04-09 CA CA000506171A patent/CA1305050C/fr not_active Expired - Lifetime
- 1986-04-15 IL IL78508A patent/IL78508A0/xx not_active IP Right Cessation
- 1986-04-16 GR GR861005A patent/GR861005B/el unknown
- 1986-04-17 ZA ZA862900A patent/ZA862900B/xx unknown
- 1986-04-17 AU AU56964/86A patent/AU594053B2/en not_active Expired
- 1986-04-17 KR KR1019860700896A patent/KR930008436B1/ko not_active Expired - Fee Related
- 1986-04-17 WO PCT/US1986/000776 patent/WO1986005950A1/fr not_active Ceased
- 1986-04-17 MX MX2200A patent/MX162186A/es unknown
- 1986-04-17 JP JP61502270A patent/JPS62502542A/ja active Granted
- 1986-04-17 BR BR8606630A patent/BR8606630A/pt not_active Application Discontinuation
- 1986-04-17 ES ES554105A patent/ES8707650A1/es not_active Expired
- 1986-04-17 EP EP86902725A patent/EP0218698A1/fr not_active Withdrawn
- 1986-04-17 TR TR201/86A patent/TR23438A/xx unknown
1987
- 1987-10-01 MY MYPI87002828A patent/MY101393A/en unknown

Also Published As

Publication number	Publication date
WO1986005950A1 (fr)	1986-10-23
AU594053B2 (en)	1990-03-01
BR8606630A (pt)	1987-08-04
JPH0523241B2 (fr)	1993-04-02
TR23438A (tr)	1989-12-29
EP0218698A1 (fr)	1987-04-22
JPS62502542A (ja)	1987-10-01
ES554105A0 (es)	1987-08-16
KR930008436B1 (ko)	1993-09-04
AU5696486A (en)	1986-11-05
ZA862900B (en)	1986-12-30
ES8707650A1 (es)	1987-08-16
GR861005B (en)	1986-08-12
MY101393A (en)	1991-10-23
KR870700290A (ko)	1987-12-28
IL78508A0 (en)	1986-08-31
MX162186A (es)	1991-04-08

Legal Events

Date	Code	Title	Description
1997-07-14	MKLA	Lapsed

Publication	Publication Date	Title
US3938986A (en)	1976-02-17	Herbicide
CA1337505C (fr)	1995-11-07	Formulations aqueuses et leur utilisation
US4814000A (en)	1989-03-21	Stabilized herbicide composition based on meta-biscarbamates
AU764924B2 (en)	2003-09-04	Solvates of pymetrozine
US5180416A (en)	1993-01-19	Herbicidal composition comprising a liquid thiocarbamate herbicide, a solid herbicide, surfactant, and dry process silicic acid
FR2706247A1 (fr)	1994-12-23	Procédé de stabilisation de compositions pesticides contenant de l'acéphate, et compositions pesticides obtenues.
US4185113A (en)	1980-01-22	Stabilized metal salts of ethylene bis dithiocarbamic acid
US4440563A (en)	1984-04-03	Thiolcarbamate sulfoxides stabilized with butyrolactone and water
US5260334A (en)	1993-11-09	Thermally stabilized bis alkylthio-alkylamino-N-alkyl carbamates
KR930008436B1 (ko)	1993-09-04	열에 안정한 비스 알킬티오-알킬이미노-n-알킬 카바메이트
US5157050A (en)	1992-10-20	Thermally stabilized bis alkylthio-alkylamino-N-alkyl carbamates
US4264777A (en)	1981-04-28	Herbicidal diphenyl ether compound
EP0001328A1 (fr)	1979-04-04	Procédé et composition pour la lutte contre les mauvaises herbes
US5691276A (en)	1997-11-25	Herbicidal composition comprising a fluoropropylthiazoline sulfonylurea derivative and another herbicide
CA1098726A (fr)	1981-04-07	Herbicide selectif
FR2478635A1 (fr)	1981-09-25	Derives de benzoxazolone, procede pour leur preparation et compositions contenant ces derives
GB2176108A (en)	1986-12-17	Stabilised liquid herbicidal compositions
GB935504A (en)	1963-08-28	Improvements in and relating to methods and compositions for regulating the growth of plants
EP0010583B1 (fr)	1981-12-16	Dérivés de 2-hydroxy-benzamide, compositions fongicides les contenant et procédé de prévention de maladies des plantes
US4853029A (en)	1989-08-01	Compositions of methyl-3-(3'methylphenyl-carbamoyloxy phenylcarbamate, stable in an aqueous emulsion
IL27724A (en)	1971-07-28	Thiaimidazolidines and their preparation
US4378990A (en)	1983-04-05	Herbicidal composition
PH26468A (en)	1992-07-27	Benzoisothiazoles and their use as pesticides
JPH05140124A (ja)	1993-06-08	トリアゾール誘導体および除草剤
JPS6153321B2 (fr)	1986-11-17